反応 #93693

ord-7ff38eea68f44483bc43bbb2373e964e

反応方程式

CC(C)(C)[Si](C)(C)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)C(=O)[C@H]5C[C@H]5[C@H]4[C@@H]3[C@H](Cl)[C@H]3O[C@]32C1
3β-(tert.-butyldimethylsilyloxy)-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one
CO
methanol
O=S(=O)(O)O
sulfuric acid
→
CC(C)OC(C)C
diisopropyl ether
C[C@]12CC[C@H]3[C@@H]([C@H](Cl)[C@H]4O[C@]45C[C@@H](O)CC[C@]35C)[C@@H]1[C@@H]1C[C@@H]1C2=O
7α-chloro-5,6β-epoxy-3β-hydroxy-15β,16β- methylene-5β-androstan-17-one

反応物

CC(C)(C)[Si](C)(C)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)C(=O)[C@H]5C[C@H]5[C@H]4[C@@H]3[C@H](Cl)[C@H]3O[C@]32C1
3β-(tert.-butyldimethylsilyloxy)-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one
CO
methanol
O=S(=O)(O)O
sulfuric acid

試薬

なし

溶媒

CCOCC
ether
C1CCOC1
tetrahydrofuran

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    洗浄washed with saturated sodium bicarbonate solution and water
  2. 2
    乾燥dried over sodium sulfate
  3. 3
    濃縮concentrated under vacuum

実験手順

142 g of 3β-(tert.-butyldimethylsilyloxy)-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one is dissolved in 400 ml of tetrahydrofuran and 400 ml of methanol and stirred with 1,000 ml of 8% strength sulfuric acid for 1.5 hours at room temperature. The mixture is then diluted with ether, washed with saturated sodium bicarbonate solution and water, dried over sodium sulfate, and concentrated under vacuum. By trituration of the resultant solid with diisopropyl ether, 108 g of 7α-chloro-5,6β-epoxy-3β-hydroxy-15β,16β- methylene-5β-androstan-17-one is obtained, mp 173° C.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US04614616uspto-grants-1986_09