13beta-Ethyl-3-methoxy-6-methyl-17,17-ethylenedioxygona-1,3,5(10),8,14-pentaene → 13-Ethyl-3-methoxy-6-methyl-17,17-ethylenedioxygona-1,3,5(10),8-tetraene

HRID 1077220Notes

Reaction equation

HRID 1077220 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:23]2[C:9]3[CH2:10][CH2:11][C@@:12]4([CH2:21][CH3:22])[C:16]([C:8]=3[CH2:7][CH:6]([CH3:26])[C:5]=2[CH:4]=1)=[CH:15][CH2:14][C:13]14[O:20][CH2:19][CH2:18][O:17]1>C1C=CC=CC=1.[Pd].C([O-])([O-])=O.[Ca+2]>[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:23]2[C:9]3[CH2:10][CH2:11][C@@:12]4([CH2:21][CH3:22])[C@H:16]([C:8]=3[CH2:7][CH:6]([CH3:26])[C:5]=2[CH:4]=1)[CH2:15][CH2:14][C:13]14[O:17][CH2:18][CH2:19][O:20]1

Participants

4

Reactant 1

HCID 6814525013beta-Ethyl-3-methoxy-6-methyl-17,17-ethylenedioxygona-1,3,5(10),8,14-pentaene

Product 1

HCID 6814418413-Ethyl-3-methoxy-6-methyl-17,17-ethylenedioxygona-1,3,5(10),8-tetraeneYield 71.5%

Reagents, catalysts & solvents 2

HCID 12000666Calcium Palladium CarbonateCatalystHCID 241BenzeneSolvent

Procedure

Monohydrogenate dl-3-methoxy-6-methyl-17,17-ethylenedioxy-13-ethylgona-1,3,5(10),8,14-pentaene (15.3 g) in benzene (300 cc) in the presence of 2% Pd/CaCO3 (5.0 g). Filter, remove the benzene under reduced pressure and recrystallize from 95% ethanol (110 cc) to yield the dl-3-methoxy-6-methyl-17,17-ethylenedioxy-13-ethylgona-1,3,5(10),8-tetraene (11.0 g), m.p. 122°-124°, diamond shaped plates, λ max. EtOH 280 mμ (ε15,140).

Workup

  1. filtrationFilter
  2. customremove the benzene under reduced pressure
  3. customrecrystallize from 95% ethanol (110 cc)

Sources & evidence

ORD record
ord-e2e222078d044a189841bd80b08c2ddc
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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