1-Chloro-3-methyl-2-butene → 1,1-Diethoxy-6-methylhept-5-EN-2-one

HRID 443373Notes

Reaction equation

[CH2:1]([O:3][CH:4]([O:13][CH2:14][CH3:15])[C:5](=[O:12])[CH2:6][C:7](OCC)=O)[CH3:2].[CH3:16][C:17]([CH3:21])=[CH:18]CCl.[O-]CC.[Na+].[OH-].[Na+]>>[CH2:14]([O:13][CH:4]([O:3][CH2:1][CH3:2])[C:5](=[O:12])[CH2:6][CH2:7][CH:16]=[C:17]([CH3:21])[CH3:18])[CH3:15]

Participants

Reactant 4

HCID 104291-Chloro-3-methyl-2-butene

HCID 14798Sodium Hydroxide

HCID 2723922Sodium ethoxide

HCID 11138577Ethyl 4,4-diethoxy-3-oxobutanoate

Product 1

HCID 132919231,1-Diethoxy-6-methylhept-5-EN-2-oneYield 57.2%

Procedure

Following the procedure stated in Referential example 1, reaction of 7.3 g of ethyl 4,4-diethoxyacetoacetate with 4.0 g of 3-methyl-2-butenyl chloride was carried out in the presence of sodium ethoxide and the resultant was decarboxylated with the alcoholic sodium hydroxide to yield 4.1 g of the desired product, b.p. 102°-103° C./ 1 mmHg.

Sources & evidence

ORD record: ord-5018b6aa0c284bd6907615d12f5313fd
Source dataset: uspto-grants-1981_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04260551

Reaction notes

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