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

HRID 1762623

Reaction equation

HRID 1762623 reaction equation
[CH3:1][C:2]1([CH3:17])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH2:10][CH:11]2[CH2:13][CH2:12]2)=[O:8])[CH:3]1[C:14]([OH:16])=[O:15].O(C1C=C([C@H](O)C)C=CC=1)C1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:17])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH2:10][CH:11]2[CH2:13][CH2:12]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][CH:10]2[CH2:11][CH2:13][CH2:12]2)=[O:8])[CH:3]1[C:14]([O-:16])=[O:15]

Participants

5

Reactant 2

HCID 22815813(1R)-1-(3-phenoxyphenyl)ethan-1-olHCID 539155962,2-Dimethyl-3-(3-cyclopropylmethoxy-3-oxo-1-propenyl) cyclopropane-carboxylic acid

Product 2

HCID 539155962,2-Dimethyl-3-(3-cyclopropylmethoxy-3-oxo-1-propenyl) cyclopropane-carboxylic acidHCID 736755712,2-Dimethyl-3-(3-cyclobutoxy-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-cyclobutoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid and 1(R)-(3-phenoxy-phenyl)-ethanol were reacted to obtain 1(R)-(3-phenoxy-phenyl)-ethyl (1R, cis, ΔZ) 2,2-dimethyl-3-(3-cyclobutoxy-3-oxo-1-propenyl)-cyclopropane-carboxylate with a specific rotation of [α]D20 =+125.5°±2° (c=1% in chloroform).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-6c1f19492d284e72bbba6e1480e15afb
Source dataset
uspto-grants-1989_05
Patent number
US04833163

Linked notes

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