Methanol → 异丙醚

HRID 65415笔记

反应方程式

HRID 65415 反应方程式
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

参与物

7

反应物 3

HCID 887MethanolHCID 1118四氧化硫HCID 130759643beta-(Tert.-butyldimethylsilyloxy)-7alpha-chloro-5,6beta-epoxy-15beta,16beta-methylene-5beta-androstan-17-one

产物 2

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

试剂、催化剂与溶剂 2

HCID 3283乙醚溶剂HCID 8028四氢呋喃溶剂

实验过程

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.

后处理

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

来源与证据

ORD记录
ord-7ff38eea68f44483bc43bbb2373e964e
来源数据集
uspto-grants-1986_09
专利号
US04614616

反应笔记

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