Acetaldehyde, 2,2-dimethoxy- → HCID 12960802, compound

HRID 354611Notes

Reaction equation

HRID 354611 reaction equation
COC(OC)C=O.[F:8]/[C:9](=[C:13](/[CH3:19])\[CH:14]([O:17][CH3:18])[O:15][CH3:16])/[C:10]([O-])=[O:11].[H-].C([Al+]CC(C)C)C(C)C>>[F:8]/[C:9](=[C:13](/[CH3:19])\[CH:14]([O:15][CH3:16])[O:17][CH3:18])/[CH:10]=[O:11]

Participants

4

Reactant 3

HCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 20494894HCID 20494894, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 12960802HCID 12960802, compound

Procedure

The 6-fluoro octatrienoate is prepared by reacting triethyl phosphono fluoroacetate with glyoxal dimethyl acetal and the resulting reaction product, a mixture of ethyl E and Z-2-fluoro-4,4-dimethoxy-3-methyl-2-butenoate, is reduced with di-isobutyl aluminum hydride in the cold to form Z-2-fluoro-3-methyl-4,4-dimethoxy-2-buten-1-al. The latter compound is then reacted via a Horner reaction with a compound of the formula ##STR38## or via a Wittig reaction with ##STR39## wherein X is halogen, to form a compound of the formula ##STR40## The latter compound is then treated with hydrochloric acid and diethyl ether to form the 6-fluoro octatrienoate depicted.

Workup

  1. customthe resulting reaction product

Sources & evidence

ORD record
ord-eff4d864d122412c816d2b13bcd81625
Source dataset
uspto-grants-1983_03
Patent number
US04375563

Reaction notes

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