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

HRID 1415048Notes

Reaction equation

HRID 1415048 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[CH:16][C:17]=4[CH:18]([CH3:20])[CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C:4]12OCC[O:23]1)[CH3:2]>CO.Cl>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[CH: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=[O:23])[CH3:2]

Participants

4

Reactant 1

HCID 68144627HCID 68144627, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Suspend dl-13-ethyl-3-methoxy-6-methyl-17,17-ethylenedioxygona-1,3,5(10)-triene (9.0 g) in methanol (200 ml) and concentrated hydrochloric acid (5 ml). Heat the mixture on a steam bath for 15 minutes. Remove the solvent under vacuum and partition the residue between ether and aqueous sodium bicarbonate. Remove the organic solvents and dry to obtain a gum. Recrystallize from methanol to obtain dl-13-ethyl-3-methoxy-6-methylgona-1,3,5(10)-trien-17-one (7.29 g), m.p. 115°-123°. Recrystallize from methanol to obtain an analytical sample with m.p. 123°-127°; ultraviolet absorption peak at 280 mμ (ε2,190), infrared maximum (potassium bromide) at 5.75 μ.

Workup

  1. temperatureHeat the mixture on a steam bath for 15 minutes
  2. customRemove the solvent under vacuum
  3. custompartition the residue between ether and aqueous sodium bicarbonate
  4. customRemove the organic solvents
  5. customdry
  6. customto obtain a gum
  7. customRecrystallize from methanol

Sources & evidence

ORD record
ord-9211039b1ee841819b5e2eaed2675cfd
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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