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G. K. S. Prakash et al.
CLUSTER
1,1,1-Trifluoro-3-tolylpropan-2-ol (3b)
–35.55, 75.84 (sept, J = 26.84 Hz), 123.07 (q, J = 287.54
Hz), 128.43, 129.013, 130.775, 131.157. 19F NMR (376.1
MHz, CDCl3): d = –76.77 (s). HRMS (EI): m/z calcd. for
C10H8OF6: 258.0479; found: 258.0477.
Ratio of o:m:p = 24:36:40. 1H NMR (400 MHz, CDCl3): d =
2.26 (s, 3 H), 2.52 (m, 1 H), 2.73 (m, 1 H), 2.96 (m, 1 H),
4.00 (m, 1 H), 7.07 (m, 4 H). 13C NMR (100 MHz, CDCl3):
d = 30.05, 35.59, 36.44, 42.26, 71.76 (q, J = 30.87 Hz),
125.076 (q, J = 281.956 Hz), 126.39, 127.57, 127.94,
128.79, 129.13, 129.23, 129.27, 129.38, 129.58, 129.76,
136.02, 141.46. 19F NMR (376.1 MHz, CDCl3): d = –80.33
(d, J = 7.63 Hz), –80.09 (d, J = 6.10 Hz), –80.04 (d, J = 6.10
Hz). HRMS (EI): m/z calcd for C10H10F3O: 204.0762; found:
204.0752.
1,1,1,3,3,3-Hexafluoro-2-(methylbenzyl)propan-2-ol (4b)
Ratio of o:m:p = 30:30:40. 1H (400 MHz, CDCl3): d = 2.35,
2.36, 2.37 (3 H), 2.78, 2.79, 2.80 (1 H), 3.24, 3.34 (4 H), 7.20
(m, 4 H). 13C NMR (100 MHz, CDCl3): d = 19.79, 21.11,
21.34, 31.81, 35.11, 35.41, 75.64 (sept, J = 28.37 Hz),
123.20 (q, J = 286.77 Hz), 126.47, 127.42, 128.18, 128.67,
129.02, 129.32, 129.84, 130.51, 131.07, 131.43, 131.88,
132.26, 138.47, 139.00. 19F NMR (376.1 MHz, CDCl3): d =
–77.14 (s), –76.82 (s), –76.78 (s). HRMS (EI): m/z calcd for
C11H10F6O: 272.0636; found: 272.0649.
2-(Ethylbenzyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (4c)
Ratio of o:m:p = 16:21:63. 1H NMR (400 MHz, CDCl3): d =
1.24 (t, J = 7.61 Hz, 3 H), 2.66 (q, J = 7.619 Hz, 2 H), 2.82,
2.85, 2.86 (m, 1 H), 3.25, 3.26, 3.36 (s, 2 H), 7.20 (m, 4 H).
13C NMR (100 MHz, CDCl3): d = 15.28, 15.41, 15.56, 25.42,
28.49, 28.74, 31.06, 35.02, 35.40, 75.63 (sept, J = 28.37 Hz),
122.99 (q, J = 288.31 Hz), 126.24, 127.51, 128.03, 128.31,
128.54, 128.83, 129.00, 129.46, 130.40, 130.67, 131.04,
132.30, 144.61, 145.22. 19F NMR (376.1 MHz, CDCl3): d =
–77.05 (s), –76.84 (s), –76.83 (s). HRMS (EI): m/z calcd. for
C12H12OF6: 286.0792; found: 286.0786.
3-Ethylphenyl-1,1,1-trifluoropropan-2-ol (3c)
Ratio of o:m:p = 30:23:47. 1H NMR (400 MHz, CDCl3): d =
1.23 (m, 3 H), 2.16 (br s, 1 H), 2.71 (m, 2 H), 2.83 (m, 1 H),
3.03 (m, 1 H), 4.15 (m appear as br s, 1 H), 7.16 (m, 4 H).
13C NMR (100 MHz, CDCl3): d = 15.19, 15.57, 25.52, 28.48,
28.78, 32.56, 35.71, 36.13, 71.46 (q, J = 30.67 Hz), 124.90
(q, J = 281.41 Hz), 126.14, 126.67, 126.81, 127.58, 128.32,
128.52, 128.78, 128.89, 129.04, 129.39, 130.35, 132.77,
143.31, 144.93. 19F NMR (376.1 MHz, CDCl3): d = –80.30
(d, J = 6.10 Hz), –80.08 (d, J = 6.10 Hz), –80.06 (d, J = 6.10
Hz). HRMS (EI): m/z calcd for C10H10F3O: 218.0918; found:
218.0909.
1,1,1-Trifluoro-3-(n-propylphenyl)propan-2-ol (3d)
Ratio of o:m:p = 31:28:41. 1H NMR (400 MHz, CDCl3): d =
0.94 (m, 3 H), 1.65 (m, 2 H), 2.23 (br s, 1 H), 2.59 (m, 2 H),
2.76 (m, 1 H), 3.02 (m, 1 H), 4.06 (m, 1 H), 7.14 (m, 4 H).
13C NMR (100 MHz, CDCl3): d 13.85, 14.13, 24.28, 24.58,
24.62, 32.60, 34.72, 35.76, 35.73, 36.14, 37.67, 37.97, 71.65
(q, J = 26.07 Hz), 124.90 (q, J = 281.41 Hz), 125.61, 126.17,
126.67, 127.38, 127.42, 128.23, 128.49, 128.69, 128.91,
129.12, 129.29, 129.662, 129.76, 130.36, 132.76, 133.49,
135.49, 141.36, 141.76, 143.40. 19F NMR (376.1 MHz,
CDCl3): d = –80.32 (d, J = 6.10 Hz), –80.08 (d, J = 7.63 Hz),
–80.06 (d, J = 6.10 Hz). HRMS (EI): m/z calcd for
C10H10F3O: 232.1075; found: 232.1077.
3-(2,5-Dimethylphenyl)-1,1,1-trifluoropropan-2-ol (3e)
1H NMR (400 MHz, CDCl3): d = 2.25 (s, 3 H), 2.29 (s, 3 H),
2.78 (dd, J1 = 10.18 Hz, J2 = 14.34 Hz, 1 H), 2.99 (dd,
J1 = 2.82 Hz, J2 = 14.27 Hz, 1 H), 4.00 (m, 1 H), 6.97 (s, 1
H), 6.98 (s, 1 H), 7.05 (d, J1 = 8.24 Hz, 1 H). 13C NMR (100
MHz, CDCl3): d = 18.99, 20.92, 33.33, 70.72 (q, J = 30.50
Hz), 125.08 (q, J = 282.17 Hz), 128.141, 130.67, 131.10,
133.66, 133.96, 135.85. 19F NMR (376.1 MHz, CDCl3): d =
80.33 (d, J = 6.10 Hz). HRMS (EI): m/z calcd for
1,1,1,3,3,3-Hexafluoro-2-(n-propylbenzyl)propan-2-ol
(4d)
Ratio of o:m:p = 33:21:46. 1H NMR (400 MHz, CDCl3): d =
0.94 (t, J = 7.33 Hz, 3 H), 1.64 (hept, J = 7.60 Hz, 2 H), 2.58
(t, J = 7.26 Hz, 2 H), 2.78, 2.81, 2.83 (1 H), 3.23, 3.24, 3.35
(2 H), 6.99–7.28 (m, 4 H). 13C NMR (100 MHz, CDCl3): d =
13.85, 14.13, 24.28, 24.56, 24.59, 24.62, 32.60, 34.72,
35.74, 36.14, 37.67, 37.97, 38.10, 71.33 (sept, J = 30.67 Hz),
124.89 (q, J = 281.41 Hz), 125.61, 126.17, 126.67, 127.38,
127.42, 128.23, 128.49, 128.69, 128.91, 129.12, 129.29,
129.662, 129.76, 130.36, 132.76, 133.49, 135.49, 141.36,
141.76,142.73, 143.40. 19F NMR (376.1 MHz, CDCl3): d =
–80.32 (d, J = 6.10 Hz), –80.08 (d, J = 7.63 Hz), –80.06 (d,
J = 6.10 Hz). HRMS (EI): m/z calcd. for C13H14OF6:
300.0949; found: 300.0957.
2-(2,5-Dimethylbenzyl)-1,1,1,3,3,3-hexafluoropropan-2-
ol (4e)
1H NMR (400 MHz, CDCl3): d = 2.30 (s, 3 H), 2.82 (s, 1 H),
3.29 (s, 2 H), 7.03–7.10 (m, 3 H). 13C NMR (100 MHz,
CDCl3): d = 19.26, 20.85, 31.76, 75.58 (sept, J = 29.14 Hz),
123.29 (q, J = 287.54 Hz), 128.72, 129.46, 131.36, 132.82,
135.71, 136.11. 19F NMR (376.1 MHz, CDCl3): d = –77.20
(s). HRMS (EI): m/z calcd for C12H12F6O: 286.0792; found:
286.0780.
C11H13F3O: 218.0918; found: 218.0918.
3-(Dimethylphenyl)-1,1,1-trifluoropropan-2-ol (3f)
Ratio of o:m:p = 11:12:77. 1H NMR (400 MHz, CDCl3): d =
2.10 (br s, 1 H), 2.24 (m, 6 H), 2.75 (dd, J1 = 10.3760 Hz,
J2 = 14.3400 Hz, 1 H), 2.98 (dd, J1 = 2.8240 Hz,
2-(Dimethylbenzyl)-1,1,1,3,3,3-hexafluoropropan-2-ol
(4f)
J2 = 14.4195 Hz, 1 H), 3.97 (m, 1 H), 6.83–7.00 (m, 3 H). 13
NMR (100 MHz, CDCl3): d = 19.35, 20.27, 20.93, 21.23,
C
Ratio of o:m:p = 14:6:80. 1H NMR (400 MHz, CDCl3): d =
2.30, 2.31, 2.36 (s, 6 H), 2.72, 2.74, 2.78 (s, 1 H), 3.18, 3.29,
3.44 (s, 2 H), 6.86–7.18 (m, 3 H). 13C NMR (100 MHz,
CDCl3): d = 19.70, 20.99, 21.22, 31.50, 35.31, 75.64 (sept,
J = 29.14 Hz), 123.34 (q, J = 288.31 Hz), 125.79, 127.27,
128.27, 128.94, 129.29, 130.26, 130.35, 132.20, 132.23,
138.56, 138.76, 138.94. 19F NMR (376.1 MHz, CDCl3): d =
–77.38 (s), –77.18 (s), –76.92 (s). HRMS (EI): m/z calcd for
C12H12F6O: 286.0792; found: 286.0786.
32.89, 70.73 (q, J = 30.500 Hz), 125.07 (q, J = 282.29 Hz),
126.98, 127.07, 127.26, 128.59, 128.93, 130.29, 131.09,
131.54, 136.63, 137.07, 138.49. 19F NMR (376.1 MHz,
CDCl3): d = –80.61 (d, J = 7.63 Hz), –80.30 (d, J = 6.10 Hz),
–80.13 (d, J = 6.10 Hz). HRMS (EI): m/z calcd for
C11H13F3O: 218.0918; found: 218.0920.
2-Benzyl-1,1,1,3,3,3-hexafluoropropan-2-ol (4a)
1H NMR (400 MHz, CDCl3): d = 2.82 (s, 1 H), 3.26 (s, 2 H),
7.26–7.36 (m, 5 H). 13C NMR (100 MHz, CDCl3): d =
Synlett 2007, No. 7, 1158–1162 © Thieme Stuttgart · New York