2,3,4,5,6-Pentafluorobenzyl Alcohol → 2,2-Dimethyl-3-(3-propoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid

HRID 1762603Notes

Reaction equation

HRID 1762603 reaction equation
[CH3:1][C:2]1([CH3:16])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH2:10][CH2:11][CH3:12])=[O:8])[CH:3]1[C:13]([OH:15])=[O:14].FC1C(F)=C(F)C(F)=C(F)C=1CO>C(Cl)(Cl)Cl>[CH3:16][C:2]1([CH3:1])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH2:10][CH2:11][CH3:12])=[O:8])[CH:3]1[C:13]([OH:15])=[O:14].[CH3:1][C:2]1([CH3:16])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH3:10])=[O:8])[CH:3]1[C:13]([O-:15])=[O:14]

Participants

5

Reactant 2

HCID 99232,3,4,5,6-Pentafluorobenzyl AlcoholHCID 545705842,2-Dimethyl-3-(3-propoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid

Product 2

HCID 545705842,2-Dimethyl-3-(3-propoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acidHCID 867430702,2-Dimethyl-3-(3-methoxy-3-oxo-1-propeny)-cyclopropane-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Using the procedure of Example 9, (1R, cis, ΔZ) 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid and (2,3,4,5,6-pentafluorophenyl)-methanol were reacted to obtain (2,3,4,5,6-pentafluoro-phenyl)methyl (1R, cis, ΔZ) 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl)-cyclopropane-carboxylate with a specific rotation of [α]D20 =+29.5°±2° (c=0.8% in chloroform).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-24f75afc5a2646d19d9852ef174bb0f1
Source dataset
uspto-grants-1989_05
Patent number
US04833163

Reaction notes

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