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

HRID 1762614Notes

Reaction equation

HRID 1762614 reaction equation
[CH3:1][C:2]1([CH3:17])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[O:8])[CH:3]1[C:14]([OH:16])=[O:15].[CH:18](Cl)(Cl)Cl>>[CH3:17][C:2]1([CH3:1])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH:10]2[CH2:11][CH2:13][CH2:18]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][CH:11]([CH3:13])[CH3:12])=[O:8])[CH:3]1[C:14]([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 6212ChloroformHCID 545483472,2-Dimethyl 3-(3-isobutoxy 3-oxo-1-propenyl) cyclopropane-1-carboxylic acid

Product 2

HCID 539623272,2-Dimethyl-3-(3-cyclobutoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acidHCID 736755752,2-Dimethyl-3-(3-isobutoxy-3-oxo-1-propenyl)-cyclopropane-carboxylate

Procedure

Using the procedure of Example 9, the product of Step C and (3-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-isobutoxy-3-oxo-1-propenyl)-cyclopropane-carboxylate with a specific rotation of [α]D20 =+20.5°±1.5° (c=1% in chloroform).

Sources & evidence

ORD record
ord-3226937394924fa3a83c965c4301492b
Source dataset
uspto-grants-1989_05
Patent number
US04833163

Reaction notes

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