tert.-butyl(1R,cis)2,2-dimethyl-3-[(Z)-2-(methoxy carbonyl)-ethenyl]-cyclopropane carboxylate → 2,2-dimethyl-3-[(Z)-2-(methoxy carbonyl)-ethenyl]-cyclopropane-carboxylic acid

HRID 1995151Notes

Reaction equation

HRID 1995151 reaction equation
[CH3:1][C:2]1([CH3:18])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH3:10])=[O:8])[C@H:3]1[C:11]([O:13]C(C)(C)C)=[O:12]>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:18])[CH:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH3:10])=[O:8])[CH:3]1[C:11]([OH:13])=[O:12]

Participants

3

Reactant 1

HCID 13253938tert.-butyl(1R,cis)2,2-dimethyl-3-[(Z)-2-(methoxy carbonyl)-ethenyl]-cyclopropane carboxylate

Product 1

HCID 545573302,2-dimethyl-3-[(Z)-2-(methoxy carbonyl)-ethenyl]-cyclopropane-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution containing 13.5 g of the product of Step B, 100 cm3 of toluene and 400 mg of hydrated p-toluene sulfonic acid was refluxed for 3 hours and then was evaporated to dryness under reduced pressure. The 11.2 g of residue were chromatographed over silica gel and was eluted with a 60-39-1 cyclohexane-ethyl acetate-acetic acid mixture. The eluate was evaporated to dryness under reduced pressure to obtain 9.6 g of (1R, cis) 2,2-dimethyl-3-[(Z)-2-(methoxy carbonyl)-ethenyl]-cyclopropane-carboxylic acid melting at 110° C. and having a specific rotation of [α]D20 =+75.4°±2° (c=1% in CHCl3).

Workup

  1. temperaturewas refluxed for 3 hours
  2. customwas evaporated to dryness under reduced pressure
  3. customThe 11.2 g of residue were chromatographed over silica gel
  4. washwas eluted with a 60-39-1 cyclohexane-ethyl acetate-acetic acid mixture
  5. customThe eluate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-129081d1dec34105a8ab49a9cd08e300
Source dataset
uspto-grants-1983_09
Patent number
US04402972

Reaction notes

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