反应详情

A mixture of t-butyldimethylsilyl chloride (29.5 g, 0.196 mole) and 5-chloro-1-pentanol (20 g, 0.163 mole) under an inert atmosphere was treated with a solution of imidazole (27.7 g, 0.407 mole) in dry DMF (40 mL). The reaction was stirred overnight at room temperature then partitioned between water (200 mL) and OEt2 l (300 mL). The aqueous layer was extracted with more OEt2 (2×100 mL), and the combined extract was dried (Na2SO4). The OEt2 was removed and the residue fractionally distilled. A small fore-run was collected (bp 57° C. (16 mm)) and then [(5-chloro-1-pentyl)oxy](1,1-dimethylethyl)dimethylsilane as a colorless oil (44.8 g, 97%): bp 120°-5° C. (17 mm), IR (film) cm-1 2960, 2940, 2900, 2865, 1475, 1465, 1390, 1365, 1290, 1260, 1110, 1055, 1030, 1010, 982, 940, 910, 840, 815, 780, 725, 660; 1H NMR (200 MHz, CDCl3) δ 3.62 (t, 6.1 Hz, 2H), 3.54 (t, 6.7 Hz, 2H), 1.79 (pentet, 7 Hz, 2H), 1.52 (m, 4H), 0.89 (s, 9H), 0.05 (s, 6H); 13C NMR (22.5 MHz, CDCl3) δ 62.8, 44.9, 32.5, 32.1, 26.0 (3C), 23.3, 18.3 (tertiary), -5.3 (2C); mass spectrum (70 eV) m/e (% base) 238, 236 (M+, not observed), 181, 179 (M+ - t-Bu., 1.0, 2.7), 125 (10.4), 123 (28.3), 95 (9.0), 93 (20.3), 75 (10.6), 73 (10.3) 70 (7.6), 69 (100.0); high resolution mass spectrum (70 eV) m/e 181.0636, 179.0656 (calculated 181.0630, 179.0660 for C7H16OClSi).

1. customthen partitioned between water (200 mL) and OEt2 l (300 mL)
2. extractionThe aqueous layer was extracted with more OEt2 (2×100 mL)
3. extractionthe combined extract
4. dry with materialwas dried (Na2SO4)
5. customThe OEt2 was removed
6. distillationthe residue fractionally distilled
7. customA small fore-run was collected (bp 57° C. (16 mm))