Ethanol → HCID 13051269、化合物

HRID 263854ノート

反応式

HRID 263854 の反応式
[OH-].[K+].[CH2:3](O)[CH3:4].C#C.[CH3:8][C@:9]12[CH2:26][CH:25]=[C:24]3[C@@H:14]([CH2:15][CH2:16][C:17]4[C@:22]3([CH3:23])[CH:21]=[CH:20][C:19](=[O:27])[CH:18]=4)[C@@H:13]1[CH2:12][CH2:11][C:10]2=[O:28]>O1CCCC1.O>[C:3]([C@:10]1([OH:28])[CH2:11][CH2:12][C@H:13]2[C@H:14]3[C@H:24]([CH2:25][CH2:26][C@:9]12[CH3:8])[C@:22]1([CH3:23])[C:17](=[CH:18][C:19](=[O:27])[CH:20]=[CH:21]1)[CH2:16][CH2:15]3)#[CH:4]

参加物

7

反応物 4

HCID 702EthanolHCID 6326AcetyleneHCID 14797Potassium HydroxideHCID 10265807Androsta-1,4,9(11)-triene-3,17-dione

生成物 1

HCID 13051269HCID 13051269、化合物収率 96.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
3 °C

実験手順

In a three-necked flask, 95 percent potassium hydroxide (200 g), tetrahydrofuran (1000 ml) and ethanol (120 ml) were stirred at 50° C. for 1 hour under a nitrogen atmosphere and then cooled to 3° C. Into the mixture prepared as above, pure dry acetylene was passed at 3° C. for 2 hours. A solution of 1,4,9(11)-androstatriene-3,17-dione (100 g) in 200 ml of dry tetrahydrofuran was added and stirred for 2 hours. The mixture was acidified with 10 percent aqueous Hcl solution, stirred under reflux for half an hour, and diluted with water. The resulting precipitated product was collected by filtration, washed with water, and dried to give 17α-ethynyl-17β-hydroxyandrosta-1,4-dien-3-one (110.3 g, purity 92.9 percent, yield 96.6 percent).

後処理

  1. stirringstirred
  2. temperatureunder reflux for half an hour
  3. customThe resulting precipitated product
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried

出典と根拠

ORDレコード
ord-2a84fc6a61d84d7ea719088bfb486062
出典データセット
uspto-grants-1997_07
特許番号
US05646136

反応ノート

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