Methyl 4-(4-oxo-chroman-3-ylidenemethyl)-benzoate → Methyl 4-chroman-3-ylmethyl-benzoate

HRID 1174593Notes

Reaction equation

HRID 1174593 reaction equation
O=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4][C:3]1=[CH:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1>CO.CC(N(C)C)=O.[Pd]>[O:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2][CH:3]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=2)[CH2:4]1

Participants

5

Reactant 1

HCID 4240115Methyl 4-(4-oxo-chroman-3-ylidenemethyl)-benzoate

Product 1

HCID 22478793Methyl 4-chroman-3-ylmethyl-benzoateYield 59.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 31374DimethylacetamideSolvent

Procedure

Pd/C 10% was added to a suspension of 260 (200 mg, 0.68 mmol) in MeOH (40 ml) and DMA (10 ml) which was previously purged under vacuum. The reaction mixture was stirred during 4 h at room temperature. After evaporation of the MeOH, water was added to the oily residue and the precipitate obtained was filtered. The crude residue was then purified by flash chromatography on silica gel (5-8% AcOEt/Hex) to afford the title compound 263 (114 mg, 59%) as a white solid. LRMS: 282.1 (Calc.); 283.0 (found).

Workup

  1. customwas previously purged under vacuum
  2. customAfter evaporation of the MeOH, water
  3. additionwas added to the oily residue
  4. customthe precipitate obtained
  5. filtrationwas filtered
  6. customThe crude residue was then purified by flash chromatography on silica gel (5-8% AcOEt/Hex)

Sources & evidence

ORD record
ord-f89f19a663564af3ad38798449a1602b
Source dataset
uspto-grants-2010_11
Patent number
US07838520B2

Reaction notes

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