Imidazole → (Tert-butyl-dimethyl-silanyloxy)-cyclopropyl-acetic acid methyl ester

To a solution of cyclopropyl-hydroxy-acetic acid methyl ester (1.00 g, 7.68 mmol) in DCM (9 mL) was added tert-butyldimethylsilyl chloride (1.27 g, 8.45 mmol) and imidazole (628 mg, 9.22 mmol). The reaction mixture was stirred at RT for 65 hours before being quenched with water (10 mL) and 1M HCl (5 mL). The mixture was extracted with ethyl acetate (3×15 mL) and the combined organic phases were washed with 1M HCl (10 mL), brine (10 mL), dried (Na2SO4) then concentrated in vacuo. This gave (tert-Butyl-dimethyl-silanyloxy)-cyclopropyl-acetic acid methyl ester as an amber oil (1.66 g, 88%). 1H NMR (400 MHz, CDCl3): δ 3.81 (1H, d, J=6.33 Hz), 3.74 (3H, s), 1.23-1.13 (1H, m), 0.89 (9H, s), 0.52-0.0.38 (4H, m), 0.06 (3H, s), 0.04 (3H, s).

1. custombefore being quenched with water (10 mL) and 1M HCl (5 mL)
2. extractionThe mixture was extracted with ethyl acetate (3×15 mL)
3. washthe combined organic phases were washed with 1M HCl (10 mL), brine (10 mL)
4. dry with materialdried (Na2SO4)
5. concentrationthen concentrated in vacuo

ORD record

ord-aa50b66a045e434a8d9f13d1feb4dc36

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09346817B2