Difluoroethanol → benzyl(1R,cis,Z)2,2-dimethyl-3-[3-oxo-3-(2,2-difluoroethoxy)-1-propenyl]-cyclopropane-carboxylate

HRID 569546Notes

Reaction equation

HRID 569546 reaction equation
[F:1][C:2]([F:5])(O)[CH3:3].[CH3:6][C:7]1([CH3:25])[C@@H:9](/[CH:10]=[CH:11]\[C:12](=[O:14])[OH:13])[C@H:8]1[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>C(Cl)(Cl)Cl>[CH3:6][C:7]1([CH3:25])[C@@H:9](/[CH:10]=[CH:11]\[C:12](=[O:13])[O:14][CH2:3][CH:2]([F:5])[F:1])[C@H:8]1[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]

Participants

4

Reactant 2

HCID 20243757DifluoroethanolHCID 86740331benzyl (1R,cis,Z) 2,2-dimethyl-3-[3-oxo-3-hydroxy-1-propenyl]-cyclopropane-carboxylate

Product 1

HCID 13335665benzyl(1R,cis,Z)2,2-dimethyl-3-[3-oxo-3-(2,2-difluoroethoxy)-1-propenyl]-cyclopropane-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Using the procedure of Example 53, difluoro-ethanol and the product of Step B of Example 57 were reacted to obtain benzyl(1R,cis,Z)2,2-dimethyl-3-[3-oxo-3-(2,2-difluoroethoxy)-1-propenyl]-cyclopropane-carboxylate with a specific rotation of [α]D20 =+52° (c=0.2% in chloroform).

Sources & evidence

ORD record
ord-e8cbe6ca0510464abceb5bd8cc0eb30c
Source dataset
uspto-grants-1988_03
Patent number
US04732903

Reaction notes

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