Hydrochloric Acid → 13-Ethyl-3-methoxy-6-methylgona-1,3,5(10)-trien-17-one

HRID 1077221Notes

Reaction equation

HRID 1077221 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:23]2[C@H:9]3[CH2:10][CH2:11][C@@:12]4([CH2:21][CH3:22])[C@H:16]([C@@H:8]3[CH2:7][CH:6]([CH3:26])[C:5]=2[CH:4]=1)[CH2:15][CH2:14][C:13]14OCC[O:17]1.Cl>CO>[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:23]2[C@H:9]3[CH2:10][CH2:11][C@@:12]4([CH2:21][CH3:22])[C@H:16]([C@@H:8]3[CH2:7][CH:6]([CH3:26])[C:5]=2[CH:4]=1)[CH2:15][CH2:14][C:13]4=[O:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68144627HCID 68144627, compound

Product 1

HCID 6814340513-Ethyl-3-methoxy-6-methylgona-1,3,5(10)-trien-17-oneYield 92.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Suspend the foregoing dl-3-methoxy-17,17-ethylenedioxy-6-methyl-13-ethylgona-1,3,5(10)-triene (9.0 g) in methanol (200 cc) and concentrated hydrochloric acid (5.0 cc) and heat on the steam bath for 15 minutes. Remove the solvent under vacuum, partition the residue between ether and aqueous sodium bicarbonate and isolate the product. Recrystallize from methanol to obtain the dl-3-methoxy-6-methyl-13-ethylgona-1,3,5(10)-trien-17-one (7.29 g), m.p. 115°-123°C. Recrystallize a small portion to obtain an analytical sample, m.p. 123°-127°C, λ max. EtOH 280 mμ, λ max. KBr 5.75 μ.

Workup

  1. customRemove the solvent under vacuum
  2. custompartition the residue between ether and aqueous sodium bicarbonate
  3. customisolate the product
  4. customRecrystallize from methanol

Sources & evidence

ORD record
ord-cf615ce15fb9475a99bcb988353ee500
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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