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

HRID 1719734Notes

Reaction equation

HRID 1719734 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 filfrate 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 filfrate 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-0ffd74569f2a42128cda8e45316efc67
Source dataset
uspto-grants-1985_09
Patent number
US04542142

Reaction notes

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