Diisopropylamine → Tert-butyl((1,2-dimethoxyprop-1-en-1-yl)oxy)dimethylsilane

Temperature

-20 °C

A solution of methyl 2-methoxypropionate (177 mg, 1.5 mmol) in THF (1 mL) was added to a solution of LDA prepared from diisopropylamine (0.212 mL, 1.50 mmol) and butyllithium (0.60 mL, 1.50 mmol) in THF (2 mL) at −78° C. under nitrogen. The mixture was gradually allowed to warm to −20° C. over 1 h, re-cooled to −78° C. and then a solution of tert-butylchlorodimethylsilane (233 mg, 1.50 mmol) in THF (1 mL) was added. The mixture was allowed to warm to rt over 2 h and stirred overnight. The reaction was quenched with satd. NaHCO3 (5 mL), diluted with DCM (10 mL). The organic layer was separated, washed with water, brine and dried (MgSO4). Evaporation of solvents afforded tert-butyl((1,2-dimethoxyprop-1-en-1-yl)oxy)dimethylsilane as a clear oil and used in the next step without further purification.

1. temperaturere-cooled to −78° C.
2. temperatureto warm to rt over 2 h
3. customThe reaction was quenched with satd
4. additionNaHCO3 (5 mL), diluted with DCM (10 mL)
5. customThe organic layer was separated
6. washwashed with water, brine
7. dry with materialdried (MgSO4)
8. customEvaporation of solvents

ORD record

ord-842df4223b95441b84cabe8d66a92937

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09326973B2