J.H. Han et al. / Tetrahedron 66 (2010) 1673–1677
1677
(3.0 mL) were added pyridine (0.73 mL, 9.0 mmol) and Ac2O
(0.34 mL, 3.6 mmol) at 0 ꢀC, and the mixture was warmed to room
temperature and stirred for 8 h. The resulting mixture was
quenched with 0.5 N HCl (3 mL) at 0 ꢀC, and extracted with Et2O
(10 mLꢂ3). The combined organic layer was washed with brine
(15 mL), dried over Na2SO4, filtered, and concentrated in vacuo.
Flash column chromatography yielded 0.29 g (66%) of 8d.17
According to the general procedure, treatment of 8d (0.24 g,
1.6 mmol) with i-Pr2NEt (0.63 mL, 3.6 mmol) and MOMCl (0.19 mL,
2.4 mmol) at 0 ꢀC, and the reaction mixture was warmed to room
temperature and stirred for 3 h. The resulting mixture was
quenched with satd NH4Cl (8 mL) at 0 ꢀC and extracted with CH2Cl2
(10 mLꢂ3). The combined organic layer was washed with brine
(15 mL), dried over Na2SO4, filtered, and concentrated in vacuo.
Flash column chromatography yielded 0.73 g (94%) of 8 g.19
According to the general procedure, treatment of 8g (1.00 g,
2.56 mmol) with i-Pr2NEt (1.01 mL, 5.63 mmol) and MOMCl
(0.29 mL, 3.8 mmol) gave 7g (1.09 g, 98%): IR (film): 2931, 1510,
2.5 mmol) gave 7d18 (0.30 g, 97%): 1H NMR (300 MHz, CDCl3)
d:
1109, 1008 cmꢁ1; 1H NMR (300 MHz, CDCl3)
d: 1.06 (s, 9H), 1.83 (m,
1.26 (s, 6H), 1.87 (t, J¼7.2 Hz, 2H), 2.04 (s, 3H), 3.37 (s, 3H), 4.20 (t,
2H), 2.66 (t, J¼8.1 Hz, 2H), 3.48 (s, 3H), 3.68 (t, J¼6.0 Hz, 2H), 5.15 (s,
J¼7.2 Hz, 2H), 4.71 (s, 2H).
2H), 6.93 (d, J¼8.7 Hz, 2H), 7.08 (d, J¼8.7 Hz, 2H), 7.39 (m, 6H), 7.66
(m, 4H); 13C NMR (75 MHz, CDCl3)
d: 19.4, 27.0, 31.3, 34.5, 56.1, 63.2,
4.1.12. ((6-(Methoxymethoxy)-6-methylheptyloxy)methyl)-benzene
(7e). To a solution of diol 7 (0.35 g, 2.4 mmol) in THF (3.0 mL), were
added NaH (60% wt in mineral oil, 87 mg, 3.6 mmol) and BnBr
(0.43 mL, 3.6 mmol) at 0 ꢀC, and the reaction mixture was allowed to
warm to room temperature and stirred for 22 h. The resulting
mixture was quenched with satd NH4Cl (8 mL) at 0 ꢀC and extracted
with CH2Cl2 (10 mLꢂ3). The combined organic layer was washed
with brine (15 mL), dried over Na2SO4, filtered, and concentrated in
vacuo. Flash column chromatography yielded 0.37 g (65%) of 8e: IR
(film): 3415, 2935, 1495, 1364, 1102, 1075 cmꢁ1; 1H NMR (300 MHz,
94.7, 116.3, 127.7, 129.5, 129.7, 134.1, 135.7, 135.8, 155.4; HRMS (FAB):
calculated for C27H35O3Si (MþþH) 435.2355; found 435.2357.
Acknowledgements
This work was supported by grants NRF-20090094024 (Priority
Research Centers Program), NRF-20080058667 (Basic Science Re-
search Program) and NRF-20090076108 (Basic Science Research
Program).
CDCl3) d: 1.20 (s, 6H), 1.38 (m, 4H), 1.45 (m, 2H), 1.64 (m, 2H), 3.47 (t,
References and notes
J¼6.6 Hz, 2H), 4.51 (s, 2H), 7.31 (m, 5H); 13C NMR (75 MHz, CDCl3)
d:
24.3, 26.9, 29.3, 29.9, 44.0, 70.5, 71.1, 73.0, 127.6, 127.8, 128.5, 138.8;
HRMS (FAB): calculated for C15H25O2 (MþþH) 237.1855; found
237.1856. According to the general procedure, treatment of 8e
(0.16 g, 0.7 mmol) with i-Pr2NEt (0.27 mL, 1.5 mmol) and MOMCl
(0.08 mL, 1.04 mmol) gave 7e (0.19 g, 96%): IR (film): 2938, 1496,
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4.50 (s, 2H), 4.70 (s, 2H); 13C NMR (75 MHz, CDCl3)
: 24.0, 26.5, 26.9,
d
´
41.9, 55.2, 70.5, 73.0, 76.4, 91.1,127.6,127.8,128.5,138.8; HRMS (FAB):
Monti, H.; Leandri, G.; Klos-Ringuet, M.; Corriol, C. Synth. Commun. 1983, 13,
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(0.32 mL, 3.0 mmol) in DMF (3.0 mL) was added NaH (0.14 g, 60%
wt in mineral oil, 3.6 mmol) at 0 ꢀC, and the mixture was stirred for
20 min at room temperature. After addition of PMBCl (0.49 mL,
3.6 mmol) the reaction mixture was stirred for 18 h at room tem-
perature. The mixture was poured into water (20 mL) and extracted
with Et2O (20 mLꢂ3). The combined organic layer was washed with
brine (15 mL), dried over Na2SO4, filtered, and concentrated in
vacuo. Flash column chromatography yielded 0.46 g (79%) of 8f: IR
(film): 3441, 2968, 1612, 1513, 1247 cmꢁ1
;
1H NMR (300 MHz,
CDCl3)
d
: 1.22 (s, 6H), 1.78 (t, J¼5.7 Hz, 2H), 3.32 (br s, 1H), 3.69 (t,
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(d, J¼8.7 Hz, 2H); 13C NMR (75 MHz, CDCl3)
d: 29.4, 41.6, 55.4, 67.5,
70.7, 73.2, 114.0, 129.5, 130.0, 159.4; HRMS (FAB): calculated for
C13H21O3 (MþþH) 225.1491; found 225.1482. According to the
general procedure, treatment of 8f (0.46 g, 2.4 mmol) with i-Pr2NEt
(0.91 mL, 5.2 mmol) and MOMCl (0.22 mL, 2.8 mmol) gave 7f
(0.54 g, 96%): IR (film) 2974, 2361, 1613, 1514, 1248, 1092,
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1033 cmꢁ1 1H NMR (300 MHz, CDCl3)
; d: 1.24 (s, 6H), 1.87 (t,
J¼7.2 Hz, 2H), 3.34 (s, 3H), 3.58 (t, J¼7.2 Hz, 2H), 3.80 (s, 3H), 4.43 (s,
2H), 4.70 (s, 2H), 6.87 (d, J¼8.7 Hz, 2H), 7.26 (d, J¼8.7 Hz, 2H); 13C
NMR (75 MHz, CDCl3) d: 24.0, 26.5, 26.9, 41.9, 55.2, 70.5, 73.0, 76.4,
91.1, 127.6, 127.8, 128.5, 138.8; HRMS (EI): calculated for C15H25O4
(MþþH) 269.1753; found 269.1750.
4.1.14. tert-Butyl(3-(4-(methoxymethoxy)phenyl)propoxy)-diphe-
nylsilane (7g). To a solution of 4-(3-hydroxypropyl)-phenol (0.30 g,
2.0 mmol) in DMF (1.5 mL) were added imidazole (0.20 mL,
3.0 mmol), DMAP (2.4 mg, 0.02 mmol), and TBDPSCl (0.62 mL,