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

HRID 569516Notes

Reaction equation

HRID 569516 reaction equation
[CH3:1][C:2]1([CH3:17])[C@@H:4]([C:5]#[C:6][C:7]([OH:9])=[O:8])[C@H:3]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].N1C2C(=CC=CC=2)C=CC=1>C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[CH3:1][C:2]1([CH3:17])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([OH:9])=[O:8])[C@H:3]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

5

Reactant 2

HCID 7047QuinolineHCID 13093787Tert.-butyl(1R,cis)2,2-dimethyl-3-(carboxy ethynyl)cyclopropane-carboxylate

Product 1

HCID 12807775tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-carboxy-ethenyl]cyclopropane-carboxylateYield 99.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2 g of 1,1-dimethylethyl(1R,cis)2,2-dimethyl-3[2-carboxyethynyl]-cyclopropane-carboxylate in 41 ml of ethyl acetate were hydrogenated in the presence of 0.38 g of 10% palladium hydroxide on barium sulfate and 0.4 ml of quinoline and the mixture was filtered. The filtrate was washed with 0.5N hydrochloric acid, then with water until neutral, dried and evaporated to dryness under reduced pressure to obtain 2 g of 1,1-dimethylethyl(1R,cis)2,2-dimethyl-3-[(Z)2-carboxyethenyl]-cyclopropane-carboxylate melting at 94° C.

Workup

  1. filtrationthe mixture was filtered
  2. washThe filtrate was washed with 0.5N hydrochloric acid
  3. dry with materialwith water until neutral, dried
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1c5483763c9a40af824aba219fb09981
Source dataset
uspto-grants-1988_03
Patent number
US04732903

Reaction notes

Loading…