2,2-Dimethyl-3-(3-cyclobutoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid → 2,2-Dimethyl-3-(3-cyclobutoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid

HRID 1762615Notes

Reaction equation

HRID 1762615 reaction equation
[CH3:1][C:2]1([CH3:17])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH:10]2[CH2:13][CH2:12][CH2:11]2)=[O:8])[CH:3]1[C:14]([OH:16])=[O:15]>C(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:17])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH:10]2[CH2:11][CH2:12][CH2:13]2)=[O:8])[CH:3]1[C:14]([OH:16])=[O:15].[CH3:17][C:2]1([CH3:1])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:3]1[C:14]([O-:16])=[O:15]

Participants

4

Reactant 1

HCID 539623272,2-Dimethyl-3-(3-cyclobutoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid

Product 2

HCID 539623272,2-Dimethyl-3-(3-cyclobutoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acidHCID 738652722,2-Dimethyl-3-(3-ethoxy-3-oxo-1-propenyl)-cyclopropane-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Using the procedure of Example 9, (1R, cis, ΔZ) 2,2-dimethyl-3-(3-ethoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid and (3d-propyn-2-yl-2,5-dioxo-imidazolidinyl)-methanol were reacted to obtain (3-propyn-2-yl-2,5-dioxo-imidazolidinyl)-methyl (1R, cis, ΔZ) 2,2-dimethyl-3-(3-ethoxy-3-oxo-1-propenyl)-cyclopropane-carboxylate with a specific rotation of [α]D20 =+10°±4° (c=0.2% in CHCl3).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-a06c18b70a424b1084ee2dd8f228bd97
Source dataset
uspto-grants-1989_05
Patent number
US04833163

Reaction notes

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