p-Toluenesulfonic acid → (1R,cis) 2,2-dimethyl-3-[Z-2-(propargyloxycarbonyl)-ethenyl]-cyclopropane-carboxylic acid

HRID 1995180Notes

Reaction equation

[CH3:1][C:2]1([CH3:20])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH2:10][C:11]#[CH:12])=[O:8])[C@H:3]1[C:13]([O:15]C(C)(C)C)=[O:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:20])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH2:10][C:11]#[CH:12])=[O:8])[C@H:3]1[C:13]([OH:15])=[O:14]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 2.0 g of the product of Step A, 0.2 g of p-toluene sulfonic acid and 20 ml of anhydrous toluene was refluxed for 10 minutes and was cooled to 0° C. and stirred for 30 minutes. The mixture was filtered and the filtrate was evaporated to dryness under reduced pressure to obtain 1.59 g of (1R,cis) 2,2-dimethyl-3-[Z-2-(propargyloxycarbonyl)-ethenyl]-cyclopropane-carboxylic acid which was used as is for the next step.

Workup

temperaturewas refluxed for 10 minutes
filtrationThe mixture was filtered
customthe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record: ord-cb102b78465e4a5d955f898e5237f867
Source dataset: uspto-grants-1983_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04402972

Reaction notes

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