Methanol → Diisopropyl Ether

HRID 1649468ノート

反応式

HRID 1649468 の反応式
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

参加物

7

反応物 3

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

生成物 2

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

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.

後処理

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

出典と根拠

ORDレコード
ord-c91238f34dbd496cbe3ba2c9677566f9
出典データセット
uspto-grants-1983_11
特許番号
US04416985

反応ノート

読み込み中…