Ethyl Acetate → HCID 22989988, compound

HRID 1169359Notes

Reaction equation

HRID 1169359 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][C:14]([C:18]([OH:20])=[O:19])=[CH:13][C:12]=3[CH:21]=2)=[CH:4][CH:3]=1.C(OCC)(=O)C.[H][H]>CO.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][CH:14]([C:18]([OH:20])=[O:19])[CH2:13][C:12]=3[CH:21]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 105646997-(4-Methylphenyl)-2,3-dihydrobenzooxepine-4-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 22989988HCID 22989988, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Into a suspension of 7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxylic acid (280 mg) in methanol (20 ml)/ethyl acetate (10 ml) was added 10% palladium on charcoal (50% water content, 70 mg). Hydrogen gas was introduced, and the resulting mixture was stirred at room temperature for 17 hours and at 50° C. for 3 hours, and was then filtered to remove the catalyst. The filtrate was concentrated, and the residue was recrystallized from ethyl acetate/hexane to obtain 7-(4-methylphenyl)-2,3,4,5-tetrahydro-1-benzooxepine-4-carboxylic acid (187 mg) as colorless crystals.

Workup

  1. filtrationwas then filtered
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated
  4. customthe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-70b62b415e984d2cb514065057e4738d
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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