Imidazole → methyl (S)-(+)-3-(t-butyldimethylsilyloxy)-2-methylpropionate

A mixture of methyl (S)-(+)-3-hydroxy-2-methylpropionate (1.00 g; 8.47 mmol) and imidazole (1.15 g; 16.9 mmol) was dissolved in anhydrous dimethylformamide (10 ml), and t-butyl-dimethylchlorosilane (1.30 g; 8.62 mmol) was added thereto at room temperature, followed by stirring at room temperature for 1.5 hours. To the reaction mixture, water (10 ml) and hexane (20 ml) were added, and after separation of the organic layer, the aqueous layer was extracted with hexane (10 ml) two times. The organic layers were combined together, washed with water (5 ml) three times and dried over anhydrous magnesium sulfate. Removal of the solvent by distillation under reduced pressure gave methyl (S)-(+)-3-(t-butyldimethylsilyloxy)-2-methylpropionate (1.91 g; yield, 97%) as a colorless oil. A portion of the oil (179 mg) was distilled by Kugelrohr® to give a purified product (176 mg) (bath temperature: 120° C./14 mmHg).

1. customat room temperature
2. customafter separation of the organic layer
3. extractionthe aqueous layer was extracted with hexane (10 ml) two times
4. washwashed with water (5 ml) three times
5. dry with materialdried over anhydrous magnesium sulfate
6. customRemoval of the solvent
7. distillationby distillation under reduced pressure

ORD record

ord-4c15dd9f94974eed978d607c9ad5e1a4

Source dataset

uspto-grants-1990_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04892961