HCID 86739003, compound → HCID 12807753, compound

HRID 1995155Notes

Reaction equation

HRID 1995155 reaction equation
[CH3:1][C:2]1([CH3:19])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH2:10][CH3:11])=[O:8])[C@H:3]1[C:12]([O:14]C(C)(C)C)=[O:13]>C1(C)C=CC=CC=1>[CH3:19][C:2]1([CH3:1])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH2:10][CH3:11])=[O:8])[C@H:3]1[C:12]([OH:14])=[O:13]

Participants

3

Reactant 1

HCID 86739003HCID 86739003, compound

Product 1

HCID 12807753HCID 12807753, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2.3 g of the product of Step C, 20 mg of hydrated p-toluene sulfonic acid and 20 ml of toluene was refluxed for 40 minutes and the mixture was then evaporated to dryness under reduced pressure. The 2.1 g of residue were chromatographed over silica gel and were eluted with a 60-39-1 cyclohexane-ethyl acetate-acetic acid mixture to obtain 1.5 g of (1R,cis) 2,2-dimethyl-3-[Z-2-(ethoxycarbonyl)-ethenyl]-cyclopropane-carboxylic acid melting at 96° C.

Workup

  1. temperaturewas refluxed for 40 minutes
  2. customthe mixture was then evaporated to dryness under reduced pressure
  3. customThe 2.1 g of residue were chromatographed over silica gel
  4. washwere eluted with a 60-39-1 cyclohexane-ethyl acetate-acetic acid mixture

Sources & evidence

ORD record
ord-a0b0db2022c246ecbef2d2da602faf3d
Source dataset
uspto-grants-1983_09
Patent number
US04402972

Reaction notes

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