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

HRID 1719774Notes

Reaction equation

HRID 1719774 reaction equation
[CH2:1]([OH:6])[C:2]([F:5])([F:4])[F:3].[CH3:7][C:8]1([CH3:26])[C@@H:10](/[CH:11]=[CH:12]\[C:13](=O)[OH:14])[C@H:9]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>>[CH3:7][C:8]1([CH3:26])[C@@H:10](/[CH:11]=[CH:12]\[C:13](=[O:14])[O:6][CH2:1][C:2]([F:5])([F:4])[F:3])[C@H:9]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

Participants

3

Reactant 2

HCID 64092,2,2-TrifluoroethanolHCID 86740331benzyl (1R,cis,Z) 2,2-dimethyl-3-[3-oxo-3-hydroxy-1-propenyl]-cyclopropane-carboxylate

Product 1

HCID 13335667benzyl(1R,cis,Z)2,2-dimethyl-3-[3-oxo-3-(2,2,2-trifluoroethoxy)-1-propenyl]-cyclopropane-carboxylate

Procedure

Using the procedure of Example 53, trifluoroethanol and the product of Step B of Example 57 were reacted to obtain benzyl (1R,cis,Z) 2,2-dimethyl-3-[3-oxo-3-(2,2,2-trifluoroethoxy)-1-propenyl]-cyclopropane-carboxylate with a specific rotation of [α]D° =+45° (c=0.6% in chloroform).

Sources & evidence

ORD record
ord-710d4b6f91504ea5a8e948bc0135c507
Source dataset
uspto-grants-1985_09
Patent number
US04542142

Reaction notes

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