(1R)-1-(3-phenoxyphenyl)ethan-1-ol → 2,2-Dimethyl-3-(3-propoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid

HRID 1762600Notes

Reaction equation

HRID 1762600 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].O(C1C=C([C@H](O)C)C=CC=1)C1C=CC=CC=1>C1C=CC=CC=1>[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].[CH3:16][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:13]([O-:15])=[O:14]

Participants

5

Reactant 2

HCID 22815813(1R)-1-(3-phenoxyphenyl)ethan-1-olHCID 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 738652722,2-Dimethyl-3-(3-ethoxy-3-oxo-1-propenyl)-cyclopropane-carboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Using the procedure of Example 9, (1R, cis, ΔZ) 2,2-dimethyl-3-(3-ethoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid and 1(R)-(3-phenoxyphenyl)-ethanol were reacted to obtain 1(R)-(3-phenoxyphenyl)-ethyl (1R, cis, ΔZ) 2,2-dimethyl-3-(3-ethoxy-3-oxo-1-propenyl)-cyclopropane-carboxylate with a specific rotation of [α]D20 =+145°±2.5° (c=1% in benzene).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-726eed7c12d34304be3d130ba199fc1c
Source dataset
uspto-grants-1989_05
Patent number
US04833163

Reaction notes

Loading…