Quinoline → (1R,cis)2,2-dimethyl-3-[Z-2-(pentyloxycarbonyl)ethenyl]-cyclopropane-carboxylic acid

HRID 1995165Notes

Reaction equation

HRID 1995165 reaction equation
[CH3:1][C:2]1([CH3:18])[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].N1C2C(=CC=CC=2)C=CC=1>C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[CH3:18][C:2]1([CH3:1])[C@@H:4](/[CH:5]=[CH: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

5

Reactant 2

HCID 7047QuinolineHCID 18599579(1R,cis)2,2-dimethyl-3-(pentyloxycarbonyl-ethynyl)-cyclopropane-carboxylic acid

Product 1

HCID 70476848(1R,cis)2,2-dimethyl-3-[Z-2-(pentyloxycarbonyl)ethenyl]-cyclopropane-carboxylic acidYield 62%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 4.8 g of the product of Step B, 50 ml of ethyl acetate, 1 ml of quinoline, 1 g of 10% palladium hydroxide on barium sulfate in 50 ml of ethyl acetate was hydrogenated and the mixture was filtered. The filtrate was washed with N hydrochloric acid, then with water, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 70-30-1 cyclohexane-ethyl acetate-acetic acid mixture to obtain 3 g of (1R,cis) 2,2-dimethyl-3-[Z-2-(pentyloxycarbonyl)-ethenyl]-cyclopropane-carboxylic acid.

Workup

  1. filtrationthe mixture was filtered
  2. washThe filtrate was washed with N hydrochloric acid
  3. dry with materialwith water, dried
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was chromatographed over silica gel
  6. washwas eluted with a 70-30-1 cyclohexane-ethyl acetate-acetic acid mixture

Sources & evidence

ORD record
ord-e1dc93adb0c34b6684332ffb842a51a1
Source dataset
uspto-grants-1983_09
Patent number
US04402972

Reaction notes

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