Ethanol → HCID 13051269, 화합물

HRID 263854노트

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HRID 263854 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 13051269HCID 13051269, 화합물수율 96.6%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
3 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2a84fc6a61d84d7ea719088bfb486062
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646136

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