HCID 68144627, compound → 13-Ethyl-3-methoxy-6-methylgona-1,3,5(10)-trien-17-one

HRID 1415041Notes

Reaction equation

HRID 1415041 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>CO.Cl>[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 1

HCID 68144627HCID 68144627, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Suspend 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 gl, m.p. 115°-123°C. Recrystallize a small portion to obtain an analytical sample, m.p. 123°-127°C, λmax. EtOH 280 mμ, λ max. KBr 5.75 μ.

Workup

  1. temperatureheat on the steam bath for 15 minutes
  2. customRemove the solvent under vacuum
  3. custompartition the residue between ether and aqueous sodium bicarbonate
  4. customisolate the product
  5. customRecrystallize from methanol

Sources & evidence

ORD record
ord-2abd960b0f0f4384bac1c9d792544a6d
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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