Water → HCID 15231284, compound

HRID 1415724Notes

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

Conditions

Temperature: 25 °C

Procedure

2.84 g (10 mmol) of androsta-1,4-diene-3,17-dione is dissolved under nitrogen atmosphere in 20 ml of anhydrous dioxane. 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 triethylaluminum in hexane is added to the reaction, so that the temperature does not rise above 30° C. Then, it is stirred for 1.5 more hours 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 more minutes. The inorganic solid is suctioned off and rewashed with 30 ml of dioxane. After concentration by evaporation of the dioxane solution, 3 g of crude product is obtained, which is chromatographed on silica gel with a hexane/ethyl acetate mixture with an increasing portion 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 melting point 168° C. is obtained.

Workup

customdoes not rise above 30° C
additionis added to the reaction
stirringthe solution is stirred for 15 more minutes
concentrationAfter concentration
customby evaporation of the dioxane solution

Sources & evidence

ORD record: ord-2bdf97b662234011bd1d879359ea4cca
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05908945

Reaction notes

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