Triethylamine → [(6-Chlorohexyl)oxy](1,1-dimethylethyl)dimethylsilane

To a stirred solution of 6-chloro-1-hexanol (8.1 g, 60 mmol), triethylamine (9.2 g, 12.7 mL, 90 mmol), and DMAP (750 mg, 0.1 equiv., 6.1 mmol) in methylene chloride (100 mL) was added tert-butyldimethylchlorosilane (10.85 g, 1.2 equiv, 72 mmol). The reaction was allowed to proceed overnight under a nitrogen atmosphere. TLC analysis in ethyl acetate indicated complete disappearance of staring alcohol (Rf =0.43) and the appearance of a new spot (Rf =0.67). The organic solution was washed with water (2×30 mL) and saturated ammonium chloride solution (1×25 mL) and dried over MgSO4. Solvents were removed by rotary evaporation and the residue distilled to afford the title compound (12.03 g, 80%) as a colorless liquid: bp 70° C./0.1 Torr; 1H NMR (200 MHz, CDCl3) δ 3.58 (2 H, t, (J=6.26 Hz), 3.50 (2 H, t, (J=6.70 Hz), 1.86-1.69 (2 H), 1.60-1.28 (6 H), 0.86 (9 H, s), 0.02 (6 H, s); mass spectrum m/z (M+) calcd for C12H27CIOSi 250.1520, found 250.1396.

1. washThe organic solution was washed with water (2×30 mL) and saturated ammonium chloride solution (1×25 mL)
2. dry with materialdried over MgSO4
3. customSolvents were removed by rotary evaporation
4. distillationthe residue distilled

ORD record

ord-7c3f3aa9bcca431dbfdc10c861e4fd13

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05686250