p-Toluenesulfonic acid → (1R,cis)2,2-dimethyl-3-(pentyloxycarbonyl-ethynyl)-cyclopropane-carboxylic acid

HRID 464456Notes

Reaction equation

HRID 464456 reaction equation
[CH3:1][C:2]1([CH3:22])[C@@H:4]([C:5]#[C:6][C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:8])[C@H:3]1[C:15]([O:17]C(C)(C)C)=[O:16].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:22][C:2]1([CH3:1])[C@@H:4]([C:5]#[C:6][C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:8])[C@H:3]1[C:15]([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 57192866tert.-butyl(1R,cis)2,2-dimethyl-3-[pentyloxycarbonylethynyl]cyclopropane-carboxylate

Product 1

HCID 18599579(1R,cis)2,2-dimethyl-3-(pentyloxycarbonyl-ethynyl)-cyclopropane-carboxylic acidYield 112%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5.24 g of the product of Step A, 50 ml of toluene and 250 mg of p-toluene sulfonic acid was refluxed until gas evolution ceased and was then evaporated to dryness under reduced pressure to obtain 4.8 g of crude (1R,cis)2,2-dimethyl-3-(pentyloxycarbonyl-ethynyl)-cyclopropane-carboxylic acid which was used as is for the next step.

Workup

  1. temperaturewas refluxed until gas evolution
  2. customwas then evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b7e3141629f848c2bf931eec41b1927f
Source dataset
uspto-grants-1985_10
Patent number
US04547522

Reaction notes

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