Water → HCID 15231284, compound
Reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@:15]3([CH3:16])[CH:14]=[CH:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:21].[CH2:22]([Al](CC)CC)[CH3:23].O>O1CCOCC1.CCCCCC.[Cu]Br>[CH2:22]([C@@H:14]1[C@@:15]2([CH3:16])[C:10]([CH2:9][CH2:8][C@@H:7]3[C@@H:17]2[CH2:18][CH2:19][C@@:2]2([CH3:1])[C@H:6]3[CH2:5][CH2:4][C:3]2=[O:21])=[CH:11][C:12](=[O:20])[CH2:13]1)[CH3:23]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 25 °C
Procedure
2.84 g (10 mmol) of androsta-1,4-diene-3,17-dione is dissolved in 20 ml of anhydrous dioxane under nitrogen atmosphere. 143 mg (1 mmol) of copper(I) bromide is added and the solution is heated to 25° C. Then 10 ml (10 mmol) of a 1 molar solution of triethyl aluminum in hexane is added to the reaction so that the temperature does not rise above 30° C. Then it is stirred for 1.5 hours more at 30° C. For hydrolysis, 1 ml of water mixed with 5 ml of dioxane is added to the reaction and the solution is stirred for 15 minutes more. The inorganic solid is suctioned off and washed again with 30 ml of dioxane. After concentration by evaporation of the dioxane solution, 3 g of crude product is obtained, that is chromatographed on silica gel with an hexane/ethyl acetate mixture with an increasing part of ethyl acetate as eluent. After concentration by evaporation of the fractions, 2.67 g of 1α-ethylandrost-4-ene-3,17-dione (85% of theory) of a melting point of 168° C. is obtained.
Workup
- customdoes not rise above 30° C
- additionis added to the reaction
- stirringthe solution is stirred for 15 minutes more
- washwashed again with 30 ml of dioxane
- concentrationAfter concentration
- customby evaporation of the dioxane solution
Sources & evidence
- ORD record
- ord-b4254efc3e2a47bc92921c8ee72a5d92
- Source dataset
- uspto-grants-1999_06
- Patent number
- US05908944
Reaction notes
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