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Potassium sodium tartarate → 3,17-Bis(ethylenedioxy)-16-fluoro-5-hydroxy-1beta-methyl-7-methylenandrostane

HRID 621624
ノート
印刷プレビュー

反応式

HRID 621624 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]1[CH2:28][O:27][CH:26]2[CH:9]([CH2:10][C:11]34[O:37][C@H:12]3[C:13](=[CH2:36])[C@@H:14]3[C@@H:23]([C@@:24]4([CH3:30])[C@@H:25]2[CH3:29])[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][C@:17]3([F:35])[O:34][CH2:33][CH2:32][O:31][CH:18]32)[O:8]1.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C(OCC)C.O1CCCC1>[CH2:7]1[CH2:28][O:27][CH:26]2[CH:9]([CH2:10][C:11]3([OH:37])[C@:24]([CH3:30])([C@@H:25]2[CH3:29])[C@@H:23]2[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]2)([CH3:20])[CH:18]2[O:31][CH2:32][CH2:33][O:34][C:17]2([F:35])[CH2:16]4)[C:13](=[CH2:36])[CH2:12]3)[O:8]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 867429553,17-Bis(ethylenedioxy)-5,6alpha-epoxy-16alpha-fluoro-1beta-methyl-7-methylenandrostane

生成物 1

HCID 867429563,17-Bis(ethylenedioxy)-16-fluoro-5-hydroxy-1beta-methyl-7-methylenandrostane

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of lithium aluminium hydride (38 mg) in diethylether (10 ml) is added gradually a solution of 3,17-bis(ethylenedioxy)-5,6α-epoxy-16α-fluoro-1β-methyl-7-methylenandrostane (431 mg) in tetrahydrofuran (10 ml). The resulting mixture is stirred at 20°-25° C. for a period of about 18 hrs after which an aqueous solution of potassium sodium tartrate is added. The mixture is filtered and concentrated to a small volume under reduced pressure. The concentrate is taken up in diethyl ether and washed well with water. The ether solution is dried over magnesium sulfate, filtered and the ether removed under vacuum to yield crude 3,17-bis(ethylenedioxy)-16-fluoro-5-hydroxy-1β-methyl-7-methylenandrostane. This intermediate is dissolved in a 2:1 mixture of acetic acid and water (5 ml) and the solution heated for 6 hrs at 40°-50° C. Then water is added and the product extracted with ethyl acetate.

後処理

  1. additionis added
  2. filtrationThe mixture is filtered
  3. concentrationconcentrated to a small volume under reduced pressure
  4. washwashed well with water
  5. dry with materialThe ether solution is dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe ether removed under vacuum

出典と根拠

ORDレコード
ord-a153d99df9df4fe4a9bed6f3732bb309
出典データセット
uspto-grants-1989_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04824830

反応ノート

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