Sodium Bicarbonate → (17beta)-13-Ethyl-3-methoxygona-1,3,5(10)-trien-17-ol

HRID 918544

反応式

HRID 918544 の反応式
C([O:5][C@@H:6]1[C@:14]2([CH2:15][CH3:16])[C@H:9]([C@@H:10]3[CH2:24][CH2:23][C:22]4[CH:21]=[C:20]([O:25][CH3:26])[CH:19]=[CH:18][C:17]=4[C@H:11]3[CH2:12][CH2:13]2)[CH2:8][CH2:7]1)(C)(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[OH:5][C@@H:6]1[C@:14]2([CH2:15][CH3:16])[C@H:9]([C@@H:10]3[CH2:24][CH2:23][C:22]4[CH:21]=[C:20]([O:25][CH3:26])[CH:19]=[CH:18][C:17]=4[C@H:11]3[CH2:12][CH2:13]2)[CH2:8][CH2:7]1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 18595372(+)-17beta-Tert.butoxy-13 beta-ethyl-3-methoxygona-1,3,5(10)-triene

生成物 1

HCID 66432(17beta)-13-Ethyl-3-methoxygona-1,3,5(10)-trien-17-ol収率 103.4%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 0.4 g (1.12 mmoles) of (+)-17β-tert.butoxy-13 β-ethyl-3-methoxygona-1,3,5(10)-triene and 0.1 g of p-toluenesulfonic acid monohydrate in 10 ml of toluene was stirred and heated at reflux for 1 hr. The resulting solution was cooled and treated with saturated aqueous sodium bicarbonate solution then extracted twice with ether. The combined organic extracts were dried, filtered and concentrated in vacuo giving 0.348 g of (+)-17β-hydroxy-13β-ethyl-3-methoxygona-1,3,5(10)-triene as a colorless solid.

後処理

  1. temperatureheated
  2. temperatureat reflux for 1 hr
  3. temperatureThe resulting solution was cooled
  4. extractionthen extracted twice with ether
  5. customThe combined organic extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e68b4df0771a4eca8c89b8a157f3a9db
出典データセット
uspto-grants-1976_07
特許番号
US03971809

関連ノート

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