tert-Butyldimethylsilyl chloride → HCID 14750109, compound

To a mixture of 45.50 g (0.323 mol) of crude 4-(hydroxymethyl)heptanenitrile and 53.5 g of t-butyldimethylsilyl chloride in 450 mL of methylene chloride at 3°-4° C., under argon, was added a solution of 67.5 mL (50.1 g, 0.388 mol) of diisopropylethylamine in 67.5 mL of methylenechloride dropwise over 10 min. 3.94 g (32.2 mmol) of 4-dimethylaminopyridine was then added and after stirring at room temperature for 66 hr, the dark reaction mixture was washed with 150 mL of 2N hydrogen chloride solution, 150 mL of water and 150 mL of saturated brine, dried (MgSO4), filtered, and concentrated. The residue was redissolved in methylene chloride, 180 g of silica gel was added and the solvent was removed under vacuum. The residual powder was placed on top of a 23/8"×9" column of 270 of silica gel and eluted, sequentially, with 1 L of hexane, 1 L of 1:19 ethyl acetate:hexane and I L of 1:9 ethyl acetate:hexane; 500-mL fractions were collected. Fractions 3-7 were combined and concentrated in vacuo, and the residue was distilled to give 68.22 g (82.9%) of 4-(t-butyldimethylsiloxymethyl)heptanenitrile, bp 114°-117° C. (0.9-1.0 mm Hg).

1. customthe dark reaction mixture
2. washwas washed with 150 mL of 2N hydrogen chloride solution, 150 mL of water and 150 mL of saturated brine
3. dry with materialdried (MgSO4)
4. filtrationfiltered
5. concentrationconcentrated
6. dissolutionThe residue was redissolved in methylene chloride
7. addition180 g of silica gel was added
8. customthe solvent was removed under vacuum
9. washeluted
10. custom500-mL fractions were collected
11. concentrationconcentrated in vacuo
12. distillationthe residue was distilled

ORD record

ord-8e8d315f8cc84128bd4e5ef9d769d7d2

Source dataset

uspto-grants-1990_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04897477