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

HRID 1762609Notes

Reaction equation

HRID 1762609 reaction equation
[CH3:1][C:2]1([CH3:17])[CH:4]([CH:5]=[CH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[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][CH2:10][CH2:13][CH3:18])=[O:8])[CH:3]1[C:14]([OH:16])=[O:15].[CH3:1][C:2]1([CH3:17])[CH:4]([CH:5]=[CH:6][C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[CH:3]1[C:14]([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 6212ChloroformHCID 542183542,2-Dimethyl-3-(3-tert.-butoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid

Product 2

HCID 545705842,2-Dimethyl-3-(3-propoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acidHCID 735089272,2-Dimethyl-3-(3-tert.-butoxy-3-oxo-1-propenyl)-cyclopropane-carboxylate

Procedure

Using the procedure of Example 9, the product of Step D and (RS) cyano 2-(6-phenoxy-pyridyl)-methanol were reacted to obtain (RS) cyano 2-(6-phenoxy-pyridyl)-methyl (1R, cis, ΔZ) 2,2-dimethyl-3-(3-tert.-butoxy-3-oxo-1-propenyl)-cyclopropane-carboxylate with a specific rotation of [α]D20 =+68°±1.5° (c=1% in chloroform).

Sources & evidence

ORD record
ord-63a50458d1934bd08436ccad1dd81b9c
Source dataset
uspto-grants-1989_05
Patent number
US04833163

Reaction notes

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