p-Toluenesulfonic acid → benzyl (1R,cis,Z) 2,2-dimethyl-3-[3-oxo-3-hydroxy-1-propenyl]-cyclopropane-carboxylate

HRID 569544Notes

Reaction equation

HRID 569544 reaction equation
[CH3:1][C:2]1([CH3:24])[C@@H:4](/[CH:5]=[CH:6]\[C:7](=[O:13])[O:8]C(C)(C)C)[C@H:3]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:24])[C@@H:4](/[CH:5]=[CH:6]\[C:7](=[O:8])[OH:13])[C@H:3]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86740330benzyl(1R,cis,Z)2,2-dimethyl-3-[3-oxo-3-tert.-butoxy-1-propenyl]-cyclopropane-carboxylate

Product 1

HCID 86740331benzyl (1R,cis,Z) 2,2-dimethyl-3-[3-oxo-3-hydroxy-1-propenyl]-cyclopropane-carboxylateYield 73.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5 g of the product of Step A, 250 mg of p-toluene sulfonic acid and 30 ml of toluene was refluxed for one hour and was cooled and chromatographed over silica gel. Elution with a 1-1 hexane-ethyl acetate mixture containing 1% of acetic acid and crystallization from isopropyl ether yielded 3.05 g of benzyl(1R,cis,Z)2,2-dimethyl-3- [3-oxo-3-hydroxy-1-propenyl]-cyclopropane-carboxylate melting at 69° C.

Workup

  1. temperaturewas refluxed for one hour
  2. temperaturewas cooled
  3. customchromatographed over silica gel
  4. washElution with a 1-1 hexane-ethyl acetate mixture
  5. additioncontaining
  6. custom1% of acetic acid and crystallization from isopropyl ether

Sources & evidence

ORD record
ord-ce68790b116d4deabfcaa64f33b41c5f
Source dataset
uspto-grants-1988_03
Patent number
US04732903

Reaction notes

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