Strontium carbonate → 13-Ethyl-3-methoxy-6-methyl-17,17-ethylenedioxygona-1,3,5(10),8-tetraene

HRID 1077226Notes

Reaction equation

HRID 1077226 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C: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:8]=3[C:7]1=[CH:6][CH2:5][C:4]12[O:26][CH2:25][CH2:24][O:23]1)[CH3:2].C(=O)([O-])[O-].[Sr+2]>C1C=CC=CC=1>[CH2:1]([C@:3]12[CH2:11][CH2:10][C: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:8]=3[C@@H:7]1[CH2:6][CH2:5][C:4]12[O:23][CH2:24][CH2:25][O:26]1)[CH3:2]

Participants

4

Reactant 2

HCID 15407Strontium carbonateHCID 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 71.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Hydrogenate dl-13β-ethyl-3-methoxy-6-methyl-17,17-ethylenedioxygona-1,3,5(10),8,14-pentaene (15.3 g) in benzene (300 ml) with 2% palladized strontium carbonate (5.0 g). The uptake of 1,040 ml. will require 10 minutes. Work up in the usual manner, then recrystallize from 95% ethanol (110 ml) to obtain dl-13β-ethyl-3-methoxy-6-methyl-17,17-ethylenedioxygona-1,3,5(10),8-tetraene (11.0 g. of diamond-shaped plates; 71.8% yield), m.p. 122°-124°; ultraviolet absorption peak at 280 mμ (ε15,140).

Workup

  1. customWork up in the usual manner, then recrystallize from 95% ethanol (110 ml)

Sources & evidence

ORD record
ord-c5e5f72ea833471dbd886ac665426e6e
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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