H. M. C. Ferraz, L. F. Silva, Jr. / Tetrahedron 57 ꢀ2001) 9939±9949
9945
J7.1 Hz, 2H), 6.34 ꢀd, J0.9 Hz, 1H), 6.99±7.16 ꢀm, 4H);
3.1.22. 2-ꢀ5,7-Dimethyl-3,4-dihydro-1-naphthalen-1-yl)-
propan-1-ol ꢀ5f). Viscous pale yellow oil; H NMR
1
3
1
C NMR ꢀ75 MHz, CDCl ) d 14.2, 15.6, 25.3, 28.2, 46.7,
3
6
1
0.6, 124.1, 126.0, 126.5, 126.8, 127.2, 128.3, 134.3, 134.8,
74.1.
ꢀ200 MHz, CDCl ) d 1.20 ꢀd, J6.9 Hz, 3H), 2.18±2.23
3
ꢀm, 2H), 2.26 ꢀs, 3H), 2.30 ꢀs, 3H), 2.48±2.76 ꢀm, 2H),
3
.08 ꢀsx, J6.5 Hz, 1H), 3.53±3.61 ꢀm, 1H), 3.69±3.77
3
.1.17. 2-ꢀ3,4-Dihydro-1-naphthalen-1-yl)-propan-1-ol
ꢀm, 1H), 5.93 ꢀt, J4.4 Hz, 1H), 6.88 ꢀs, 1H), 7.03 ꢀs,
1
1H); C NMR ꢀ50 MHz, CDCl ) d 17.1, 19.8, 21.2, 22.8,
3
ꢀ
3
ꢀ
5a). General procedure for the preparation of the
-alkenols 5a±p. To a stirred suspension of LiAlH4
3.24 g, 85.0 mmol) in anhydrous THF ꢀ85 mL) was added
3
23.6, 36.4, 66.9, 121.0, 123.8, 129.7, 132.2, 134.4, 134.8,
134.9, 138.2.
dropwise, over a period of 30 min and at 08C, a solution of
the ester 4a ꢀ19.7 g, 85.4 mmol) in anhydrous THF ꢀ85 mL).
The mixture was stirred at room temperature for 2 h and
water was carefully added dropwise, followed by 10%
aqueous H SO . The aqueous phase was extracted two
3.1.23. 2-ꢀ4-Methyl-3,4-dihydro-1-naphthalen-1-yl)-pro-
pan-1-ol ꢀ5g). Viscous colorless oil; H NMR ꢀ200 MHz,
CDCl ) d 1.17±1.25 ꢀm, 6H), 1.99±2.19 ꢀm, 1H), 2.35±2.53
3
1
ꢀm, 1H), 2.78±2.91 ꢀm, 1H), 3.09 ꢀsx, J6.5 Hz, 1H), 3.53±
2
4
times with ethyl acetate, washed with brine and dried over
anhydrous MgSO . The solvent was removed under reduced
3.63 ꢀm, 1H), 3.71±3.80 ꢀm, 1H), 5.81±5.89 ꢀm, 1H), 7.18±
7.24 ꢀm, 3H), 7.32±7.37 ꢀm, 1H); C NMR ꢀ50 MHz,
1
3
4
pressure giving the alkenol 5a ꢀ15.9 g, 84.4 mmol, 99%):
viscous colorless oil; H NMR ꢀ200 MHz, CDCl ) d 1.22 ꢀd,
CDCl ) d 16.8, 17.0, 19.5, 20.0, 30.7, 30.9, 32.1, 36.3,
3
1
66.7, 66.8, 122.2, 122.3, 122.4, 122.6, 126.1, 126.19,
126.25, 126.6, 127.1, 133.6, 133.8, 137.2, 137.5, 141.7,
141.9.
3
J6.9 Hz, 3H), 2.22±2.33 ꢀm, 2H), 2.68±2.76 ꢀm, 2H), 3.09
ꢀ
sx, J6.5 Hz, 1H), 3.55±3.64 ꢀm, 1H), 3.71±3.79 ꢀm, 1H),
1
.94 ꢀm, 1H), 7.14±7.34 ꢀm, 4H); C NMR ꢀ50 MHz,
3
5
CDCl ) d 16.9, 23.0, 28.4, 36.3, 66.7, 122.2, 124.2, 126.4,
3.1.24. 2-ꢀ3,4-Dihydro-1-naphthalen-1-yl)-butan-1-ol ꢀ5h).
Viscous colorless oil; H NMR ꢀ300 MHz, CDCl ) d 0.92 ꢀt,
3
1
1
26.8, 127.8, 134.6, 137.0, 138.0.
3
J7.4 Hz, 3H), 1.51±1.74 ꢀm, 3H), 2.25±2.31 ꢀm, 2H), 2.72
ꢀm, 2H), 2.88 ꢀquintet, J6.3 Hz, 1H), 3.63±3.77 ꢀm, 2H),
5.93 ꢀt, J4.7 Hz, 1H), 7.13±7.24 ꢀm, 3H), 7.33 ꢀd, J
3.1.18. 2-ꢀ6-Methoxy-3,4-dihydro-1-naphthalen-1-yl)-
propan-1-ol ꢀ5b). White solid; mp: 678C; H NMR
1
1
3
ꢀ
ꢀ
300 MHz, CDCl ) d 1.19 ꢀd, J6.9 Hz, 3H), 2.19±2.29
7.5 Hz, 1H); C NMR ꢀ75 MHz, CDCl ) d 11.8, 23.1,
3
3
m, 2H), 2.68 ꢀt, J6.8 Hz, 2H), 3.01 ꢀsx, J6.5 Hz, 1H),
24.1, 28.6, 43.9, 65.2, 122.4, 124.8, 126.4, 126.8, 127.8,
135.2, 136.8.
3
5
1
5
1
.51±3.57 ꢀm, 1H), 3.69±3.74 ꢀm, 1H), 3.78 ꢀs, 3H),
.78±5.81 ꢀm, 1H), 6.66±6.73 ꢀm, 2H), 7.22±7.25 ꢀm,
H); C NMR ꢀ75 MHz, CDCl ) d 16.9, 23.0, 28.9, 36.5,
1
3
3.1.25. 2-ꢀ6-Methoxy-3,4-dihydro-1-naphthalen-1-yl)-
butan-1-ol ꢀ5i). Viscous pale yellow oil; H NMR
3
1
5.2, 66.8, 110.9, 114.0, 121.6, 123.5, 127.7, 137.7, 138.8,
58.5.
ꢀ300 MHz, CDCl ) d 0.92 ꢀt, J7.4 Hz, 3H), 1.49±1.74
3
ꢀ
m, 2H), 1.8 ꢀbr s, 1H), 2.22±2.29 ꢀm, 2H), 2.70 ꢀt, J
3
.1.19.
propan-1-ol ꢀ5c). Pale yellow solid; mp: 658C; H NMR
2-ꢀ5-Methoxy-3,4-dihydro-1-naphthalen-1-yl)-
7.9 Hz, 2H), 2.83 ꢀquintet, J6.4 Hz, 1H), 3.61±3.78 ꢀm,
1
2H), 3.79 ꢀs, 3H), 5.80 ꢀt, J4.5 Hz, 1H), 6.70±6.74 ꢀm,
1
2H), 7.23±7.26 ꢀm, 1H); C NMR ꢀ75 MHz, CDCl ) d
3
ꢀ
2
300 MHz, CDCl ) d 1.18 ꢀd, J6.9 Hz, 3H), 2.16±2.28 ꢀm,
3
3
H), 2.57±2.68 ꢀm, 1H), 2.76±2.86 ꢀm, 1H), 3.02 ꢀsx,
11.8, 23.0, 24.0, 29.1, 44.0, 55.2, 65.1, 110.9, 114.0,
122.3, 123.6, 128.3, 136.4, 138.9, 158.4.
J6.5 Hz, 1H), 3.53±3.58 ꢀm, 1H), 3.70±3.75 ꢀm, 1H),
3
6
.83 ꢀs, 3H), 5.93±5.96 ꢀm, 1H), 6.78 ꢀd, J8.2 Hz, 1H),
1
3
.98 ꢀd, J7.8 Hz, 1H), 7.15 ꢀt, J8.0 Hz, 1H); C NMR
3.1.26. 2-ꢀ6-Methoxy-3,4-dihydro-1-naphthalen-1-yl)-
ethan-1-ol ꢀ5k). Viscous pale yellow oil; H NMR
1
ꢀ
75 MHz, CDCl ) d 17.0, 19.9, 22.5, 36.7, 55.6, 66.9, 109.7,
3
1
15.3, 124.4, 125.0, 126.4, 135.8, 137.9, 156.2.
ꢀ300 MHz, CDCl ) d 1.99 ꢀbr s, 1H), 2.20±2.27 ꢀm, 2H),
3
2
.66±2.74 ꢀm, 4H), 3.74 ꢀt, J6.6 Hz, 2H), 3.78 ꢀs, 3H),
3.1.20. 2-ꢀ7-Methoxy-3,4-dihydro-1-naphthalen-1-yl)-
propan-1-ol ꢀ5d). Pale yellow oil; H NMR ꢀ300 MHz,
5.80 ꢀt, J4.5 Hz, 1H), 6.68±6.71 ꢀm, 2H), 7.14±7.17 ꢀm,
1
13
1H); C NMR ꢀ75 MHz, CDCl ) d 23.1, 28.9, 36.1, 55.2,
61.2, 110.9, 114.0, 123.8, 124.8, 127.4, 132.4, 138.6, 158.5.
3
CDCl ) d 1.21 ꢀd, J6.9 Hz, 3H), 2.21±2.28 ꢀm, 2H),
3
2
3
.65 ꢀt, J7.9 Hz, 2H), 3.03 ꢀsx, J6.6 Hz, 1H), 3.56±
.62 ꢀm, 1H), 3.71±3.77 ꢀm, 1H), 3.80 ꢀs, 3H), 5.95±5.98
3.1.27. 2-ꢀ5-Methoxy-3,4-dihydro-1-naphthalen-1-yl)-
ethan-1-ol ꢀ5l). Viscous colorless oil;
1
ꢀ
m, 1H), 6.70 ꢀdd, J2.6 and 8.2 Hz, 1H), 6.90 ꢀd, J
H
NMR
ꢀ300 MHz, CDCl ) d 2.21±2.28 ꢀm, 2H), 2.70±2.78 ꢀm,
1
3
2
CDCl ) d 17.0, 23.4, 27.5, 36.5, 55.3, 68.4, 109.4, 110.9,
1
.6 Hz, 1H), 7.07 ꢀd, J8.2 Hz, 1H); C NMR ꢀ75 MHz,
3
4H), 3.76 ꢀt, J6.4 Hz, 2H), 3.83 ꢀs, 3H), 5.96 ꢀt, J
3
24.8, 128.3, 129.2, 135.7, 138.0, 158.4.
4.5 Hz, 1H), 6.80 ꢀd, J8.2 Hz, 1H), 6.91 ꢀd, J7.7 Hz,
1
H), 7.13±7.19 ꢀm, 2H); C NMR ꢀ75 MHz, CDCl ) d
3
1
3
3.1.21. 2-ꢀ6,7-Dimethoxy-3,4-dihydro-1-naphthalen-1-yl)-
propan-1-ol ꢀ5e). Viscous pale yellow oil; H NMR
20.0, 22.5, 36.4, 55.6, 61.3, 109.8, 115.6, 124.7, 126.5,
127.8, 132.6, 135.3, 156.3.
1
ꢀ
ꢀ
3
200 MHz, CDCl ) d 1.20 ꢀd, J6.9 Hz, 3H), 2.18±2.29
3
m, 2H), 2.60±2.68 ꢀm, 2H), 3.02 ꢀsx, J6.5 Hz, 1H),
3.1.28. 2-ꢀ7-Methoxy-3,4-dihydro-1-naphthalen-1-yl)-
ethan-1-ol ꢀ5m). Viscous pale yellow oil; H NMR
1
.55±3.63 ꢀm, 1H), 3.70±3.78 ꢀm, 1H), 3.87 ꢀs, 3H), 3.88
ꢀ
s, 3H), 5.84 ꢀt, J4.5 Hz, 1H), 6.71 ꢀs, 1H), 6.90 ꢀs, 1H);
ꢀ300 MHz, CDCl ) d 1.84 ꢀbr s, 1H), 2.12±2.18 ꢀm, 2H),
3
1
3
C NMR ꢀ50 MHz, CDCl ) d 17.0, 23.2, 28.1, 36.6, 56.0,
3
2.55±2.63 ꢀm, 4H), 3.66±3.70 ꢀm, 2H), 3.69 ꢀs, 3H), 5.86 ꢀt,
J4.5 Hz, 1H), 6.59 ꢀdd, J2.6 and 8.2 Hz, 1H), 6.74 ꢀd,
5
1
6.3, 66.8, 107.1, 111.6, 122.0, 127.4, 129.9, 137.7, 147.3,
47.7.
1
3
J2.6, 1H), 6.96 ꢀd, J8.2 Hz, 1H); C NMR ꢀ75 MHz,