HCID 90229424, compound → HCID 90229297, compound

HRID 1505751Notes

Reaction equation

HRID 1505751 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][CH:13]2[CH2:15][CH2:14]2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH:13]2[CH2:15][CH2:14]2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 1

HCID 90229424HCID 90229424, compound

Product 1

HCID 90229297HCID 90229297, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-5-(cyclopropylethynyl)benzoic acid (200 mg) in ethyl acetate (20 mL) was added 10% palladium on carbon (40 mg), and the mixture was stirred under hydrogen atmosphere (0.2 MPa) for 14 hours, then was filtered off on celite, and the mother liquor was concentrated in vacuo. The residue was purified on silica gel column chromatography to obtain the titled compound (190 mg) as yellow oil.

Workup

  1. filtrationwas filtered off on celite
  2. concentrationthe mother liquor was concentrated in vacuo
  3. customThe residue was purified on silica gel column chromatography

Sources & evidence

ORD record
ord-d5afb806486744588f8d860b79745b7c
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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