Ethanol → HCID 13051269, compound

HRID 263854Notes

Reaction equation

HRID 263854 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 13051269HCID 13051269, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
3 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-2a84fc6a61d84d7ea719088bfb486062
Source dataset
uspto-grants-1997_07
Patent number
US05646136

Reaction notes

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