Benzyl Bromide → benzyl(1R,cis,Z)2,2-dimethyl-3-[3-oxo-3-tert.-butoxy-1-propenyl]-cyclopropane-carboxylate

温度

15 °C

A solution of 25 g of (1R,cis,Z) 2,2-dimethyl-3-[3-oxo-3-tert.-butoxy-1-propenyl]-cyclopropane-carboxylic acid in 250 ml of tetrahydrofuran were added at 10° C. to a mixture of 2.6 g of sodium hydride in 100 ml of tetrahydrofuran and the mixture was stirred at 15° C. for 30 minutes. A solution of 35 ml of benzyl bromide in 100 ml of tetrahydrofuran was added to the mixture which was heated at 50° C. for 48 hours and then was cooled and poured into aqueous monosodium phosphate solution. The mixture was extracted with isopropyl ether and the organic phase was washed with water, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 9-1 hexane-isopropyl ether mixture to obtain 30 g of benzyl (1R,cis,Z) 2,2-dimethyl-3-[3-oxo-3-tert.-butoxy-1-propenyl]-cyclopropane-carboxylate.

1. temperaturewas heated at 50° C. for 48 hours
2. temperaturewas cooled
3. extractionThe mixture was extracted with isopropyl ether
4. washthe organic phase was washed with water
5. customdried
6. customevaporated to dryness under reduced pressure
7. customThe residue was chromatographed over silica gel
8. washwas eluted with a 9-1 hexane-isopropyl ether mixture

ORDレコード

ord-135eabfa38994b3c91256e32e5a0bd21

出典データセット

uspto-grants-1989_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04883806