반응 #93697

ord-1b5da12675b84083aa07322770628b90

반응 방정식

C[C@]12CC[C@H]3[C@@H]([C@H](Cl)[C@H]4O[C@]45C[C@@H](O[Si](Cc4ccccc4)(Cc4ccccc4)Cc4ccccc4)CC[C@]35C)[C@@H]1[C@@H]1C[C@@H]1C2=O
3β-tribenzylsilyloxy-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

반응물

C[C@]12CC[C@H]3[C@@H]([C@H](Cl)[C@H]4O[C@]45C[C@@H](O[Si](Cc4ccccc4)(Cc4ccccc4)Cc4ccccc4)CC[C@]35C)[C@@H]1[C@@H]1C[C@@H]1C2=O
3β-tribenzylsilyloxy-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one
CO
methanol
O=S(=O)(O)O
sulfuric acid

시약

없음

용매

CCOCC
ether
C1CCOC1
tetrahydrofuran

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    세척washed with saturated sodium bicarbonate solution and water
  2. 2
    건조dried over sodium sulfate
  3. 3
    농축concentrated under vacuum

실험 절차

19 g of 3β-tribenzylsilyloxy-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one is dissolved in 50 ml of tetrahydrofuran and 50 ml of methanol and agitated with 15 ml of 8% sulfuric acid for 2 hours at room temperature. The mixture is thereafter diluted with ether, washed with saturated sodium bicarbonate solution and water, dried over sodium sulfate, and concentrated under vacuum. By trituration of the thus-obtained solid with diisopropyl ether, 8.7 g of 7α-chloro-5,6β-epoxy-3β-hydroxy-15β,16β-methylene-5β-androstan-17-one is obtained, mp 172° C.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US04614616uspto-grants-1986_09