Hydrochloric Acid → HCID 86733489, compound

HRID 1415052Notes

Reaction equation

HRID 1415052 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH2:13][CH:14]=[C:15]([O:21]C)[CH2:16][C:17]=4[CH:18]([CH3:20])[CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@:4]2([C:24]#[CH:25])[OH:23])[CH3:2].Cl.O>CO>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([C@@H:18]([CH3:20])[CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@:4]2([C:24]#[CH:25])[OH:23])=[CH:16][C:15](=[O:21])[CH2:14][CH2:13]4)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 8673348813-Ethyl-3-methoxy-17alpha-ethynyl-17-hydroxy-6-methylgona-2,5(10)-diene

Product 1

HCID 86733489HCID 86733489, compoundYield 17.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve dl-13-ethyl-3-methoxy-6-methyl-17α-ethynyl-17-hydroxygona-2,5(10)-diene (3.5 g) in methanol (90 ml) containing concentrated hydrochloric acid (6.0 ml) and water (4.0 ml). Stir the solution under nitrogen for 1 hour. Work up in the usual fashion. Chromatograph on Florex (150 g), then recrystallize from ether-hexane to obtain dl-13-ethyl-17α-ethynyl-17-hydroxy-6α-methylgon-4-en-3-one (0.60 g), m.p. 148°-151°; ultraviolet absorption peak at 240 mμ (ε15,300), infrared maxima (chloroform) at 2.55 μ, 3.05 μ, 6.01 μ.

Workup

  1. customChromatograph on Florex (150 g), then recrystallize from ether-hexane

Sources & evidence

ORD record
ord-146c84a160724932b8a6d38185f797c5
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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