Hydrochloric Acid → HCID 86733489, compound

HRID 1415039Notes

Reaction equation

HRID 1415039 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

Stir dl-13-ethyl-3-methoxy-17α-ethynyl-17-hydroxy-6-methylgona-2,5(10)-diene (3.5 g) in methanol (90 cc) containing hydrochloric acid (60 cc) and water (4.0 ml) under nitrogen for 1 hour. Isolate the crude product, chromatograph on Florex (150 g) and recrystallize from ethyl acetate-hexane to obtain the title compound (0.60 g), m.p. 148°-151°, λmax. CHCl3 2.55 μ, 3.05 μ, 6.01 μ; λmax. EtOH 240 mμ (ε15,100).

Workup

  1. customIsolate the crude product, chromatograph on Florex (150 g)
  2. customrecrystallize from ethyl acetate-hexane

Sources & evidence

ORD record
ord-8389fb11caad46c88e8e4a6b88fd34d9
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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