Ethyl chloroformate → Ethyl 4-(trimethylsilyloxy)-2-butynoate

To a solution of trimethyl(prop-2-ynyloxy)silane (15 ml) in tetrahydrofuran (100 ml) was added butyllithium (2.6 M in hexane, 38 ml) at −78° C. The resulting mixture was stirred at the same temperature for 0.5 hour, and ethyl chloroformate (10 ml) was added thereto. The resulting mixture was stirred at −78° C. for 1.5 hours, and poured into ice water. The resulting materials were extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride solution successively. The extract was dried over anhydrous sodium sulfate, and the solvents were evaporated in vacuo to afford ethyl 4-(trimethylsilyloxy)but-2-ynoate (16.5 g).

1. stirringThe resulting mixture was stirred at −78° C. for 1.5 hours
2. extractionThe resulting materials were extracted with ethyl acetate
3. washThe organic layer was washed with water and saturated aqueous sodium chloride solution successively
4. dry with materialThe extract was dried over anhydrous sodium sulfate
5. customthe solvents were evaporated in vacuo

ORD record

ord-5980a8cf82184cb18a193aa02aa531c6

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07829580B2