Hydrochloric Acid → 16-Ethylidene-3-methoxy-1,3,5(10)-estratrien-17-one

HRID 1154781Notes

Reaction equation

CN([CH:4]=[C:5]1[CH2:10][C@H:9]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:7]2([CH3:8])[C:6]1=[O:25])[C:19]1[CH:18]=[CH:17][C:16]([O:23][CH3:24])=[CH:15][C:14]=1[CH2:13][CH2:12]3)C.[C:26]1(C)C=CC=CC=1.C[Li].Cl>CCOCC.O>[CH:4](=[C:5]1[CH2:10][C@H:9]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:7]2([CH3:8])[C:6]1=[O:25])[C:19]1[CH:18]=[CH:17][C:16]([O:23][CH3:24])=[CH:15][C:14]=1[CH2:13][CH2:12]3)[CH3:26]

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of 5 g. of 16-dimethylaminomethylene-3-methoxy-1,3,5(10)-estratrien-17-one in 150 ml. of toluene is combined dropwise at -10° C. with 28.5 ml. of a 5% solution of methyllithium in ether. After this dropwise addition, the mixture is agitated for 15 minutes at -10° C.; then about 10 ml. of water is gently added in drops, and the reaction solution is poured into about 200 ml. of 0.5 N hydrochloric acid. The organic phase is separated, dried over sodium sulfate, and concentrated under vacuum. After crystallization of the residue from ethyl acetate/ether, 3.9 g. of 16-ethylidene-3-methoxy-1,3,5(10)-estratrien-17-one is obtained, m.p. 139°-140° C.

Workup

customis combined dropwise at -10° C. with 28.5 ml
additionAfter this dropwise addition
additionthe reaction solution is poured into about 200 ml
customThe organic phase is separated
dry with materialdried over sodium sulfate
concentrationconcentrated under vacuum
customAfter crystallization of the residue from ethyl acetate/ether, 3.9 g

Sources & evidence

ORD record: ord-3d1d44b2e1854f22b52cd720250ac87d
Source dataset: uspto-grants-1981_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04298538

Reaction notes

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