Hydrochloric Acid → HCID 86733489, compound

HRID 1077219Notes

Reaction equation

HRID 1077219 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 one 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°, λ max. CHCl3 2.55 μ, 3.05 μ, 6.01 μ; λ max. EtOH 240 mμ (ε15,000).

Workup

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

Sources & evidence

ORD record
ord-7a5e7903269041d3807c30d732267b14
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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