Quinoline → tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-carboxy-ethenyl]cyclopropane-carboxylate

HRID 1995156Notes

Reaction equation

HRID 1995156 reaction equation
[CH3:1][C:2]1([CH3:14])[CH:4](/[CH:5]=[CH:6]\[C:7]([O:9]C)=[O:8])[CH:3]1[C:11]([OH:13])=[O:12].N1[C:24]2[C:19](=[CH:20]C=CC=2)[CH:18]=CC=1>[OH-].[Pd+2].[OH-].C(OCC)(=O)C>[CH3:1][C:2]1([CH3:14])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([OH:9])=[O:8])[C@H:3]1[C:11]([O:13][C:19]([CH3:24])([CH3:20])[CH3:18])=[O:12]

Participants

5

Reactant 2

HCID 7047QuinolineHCID 545573302,2-dimethyl-3-[(Z)-2-(methoxy carbonyl)-ethenyl]-cyclopropane-carboxylic acid

Product 1

HCID 12807775tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-carboxy-ethenyl]cyclopropane-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2 g of tert.-butyl (1R, cis) 2,2-dimethyl-3-[Z-carboxyethynyl]-cyclopropane-carboxylic acid, 40 ml of ethyl acetate, 0.38 g of 10% palladium hydroxide on barium sulfate and 0.4 ml of quinoline was hydrogenated and was filtered. The filtrate was washed with 0.5 N hydrochloric acid and with water until the wash water was neutral, dried and evaporated to dryness under reduced pressure to obtain 2 g of tert.-butyl (1R,cis) 2,2-dimethyl-3-[Z-2-carboxyethenyl]-cyclopropane-carboxylate melting at 94° C.

Workup

  1. filtrationwas filtered
  2. washThe filtrate was washed with 0.5 N hydrochloric acid and with water until the wash water
  3. customdried
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-ed435e250fa74f5e928b60f233fff407
Source dataset
uspto-grants-1983_09
Patent number
US04402972

Reaction notes

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