Methanol → Diisopropyl Ether

HRID 1649468노트

반응식

HRID 1649468 반응식
C([Si](C)(C)[O:6][C@H:7]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@:9]3([O:29][C@@H:10]3[C@@H:11]([Cl:28])[C@@H:12]3[C@@H:21]2[CH2:20][CH2:19][C@@:17]2([CH3:18])[C@H:13]3[C@@H:14]3[CH2:27][C@@H:15]3[C:16]2=[O:26])[CH2:8]1)(C)(C)C.[CH3:32]O.S(=O)(=O)(O)O>O1CCCC1.CCOCC>[CH:10]([O:29][CH:9]([CH3:8])[CH3:22])([CH3:11])[CH3:32].[Cl:28][C@@H:11]1[C@H:10]2[O:29][C@:9]32[C@:22]([CH3:25])([CH2:23][CH2:24][C@H:7]([OH:6])[CH2:8]3)[C@@H:21]2[C@@H:12]1[C@H:13]1[C@@:17]([CH2:19][CH2:20]2)([CH3:18])[C:16](=[O:26])[C@H:15]2[CH2:27][C@@H:14]12

참가 물질

7

반응물 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 130759643beta-(Tert.-butyldimethylsilyloxy)-7alpha-chloro-5,6beta-epoxy-15beta,16beta-methylene-5beta-androstan-17-one

생성물 2

HCID 7914Diisopropyl EtherHCID 130759667alpha-Chloro-5,6beta-epoxy-3beta-hydroxy-15beta,16beta-methylene-5beta-androstan-17-one

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  1. washwashed with saturated sodium bicarbonate solution and water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-c91238f34dbd496cbe3ba2c9677566f9
출처 데이터셋
uspto-grants-1983_11
특허 번호
US04416985

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