3,7,11-Trimethyldodeca-1,6,10-trien-3-ol → (Z,E)-1,1-Dimethoxy-6,10,14-trimethyl-5,9,13-pentadecatrien-2-one

HRID 443377Notes

Reaction equation

HRID 443377 reaction equation
[CH2:1](Br)[CH:2]=[C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH3:9])[CH3:4].OC(CCC=C(CCC=C(C)C)C)(C=C)C.[CH3:33][O:34][CH:35]([O:43][CH3:44])[C:36](=[O:42])[CH2:37]C(OC)=O>>[CH3:33][O:34][CH:35]([O:43][CH3:44])[C:36](=[O:42])[CH2:37][CH2:1]/[CH:2]=[C:3](/[CH3:4])\[CH2:5][CH2:6]/[CH:7]=[C:8](\[CH3:9])/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14]

Participants

4

Reactant 3

HCID 88883,7,11-Trimethyldodeca-1,6,10-trien-3-olHCID 550199Farnesyl bromideHCID 11008445Methyl 4,4-dimethoxy-3-oxobutanoate

Product 1

HCID 86735220(Z,E)-1,1-Dimethoxy-6,10,14-trimethyl-5,9,13-pentadecatrien-2-one

Procedure

Following the procedure stated in Referential example 1, reaction of farnesyl bromide which had been prepared from 22 g of nerolidol with 19 g of methyl 4,4-dimethoxyacetoacetate was carried out and the reaction mixture was purified by the silica gel (200 g) column chromatography to yield 12.8 g of the desired product.

Workup

  1. customthe reaction mixture was purified by the silica gel (200 g) column chromatography

Sources & evidence

ORD record
ord-cd8c78ad5f594abba40714ef1e83c823
Source dataset
uspto-grants-1981_04
Patent number
US04260551

Reaction notes

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