Methyl 4-[2-(2-benzyloxy-3-pyridyl)ethenyl]benzoate → 4-[2-(2-Benzyloxy-3-pyridyl)ethyl]benzoic acid

HRID 2395064Notes

Reaction equation

HRID 2395064 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH:15]=[CH:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=2)=[CH:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.[Rh]>[CH2:1]([O:8][C:9]1[C:14]([CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:25][CH:26]=2)=[CH:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 53806701Methyl 4-[2-(2-benzyloxy-3-pyridyl)ethenyl]benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 189739644-[2-(2-Benzyloxy-3-pyridyl)ethyl]benzoic acidYield 51.7%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent2×

Procedure

A suspension of rhodium on alumina (5%, 0.1 g) in ethanol (20 ml) was flushed well with argon. A solution of the methyl 4-[2-(2-benzyloxypyrid-3-yl)ethenyl]benzoate (1.0 g, 2.9 mmol) in ethanol (60 ml) was added. The reaction was transferred to a manometer under an atmosphere of hydrogen and the reaction was stirred at ambient temperature until 1.4 equivalents hydrogen had been taken up. The reaction mixture was filtered and evaporated and the residue subjected to chromatography on SiO2 (CH2Cl2 /hexane) to give 4-[2-(2-benzyloxypyrid-3-yl)ethyl]benzoic acid (0.5 g, 49%).

Workup

  1. customwas flushed well with argon
  2. filtrationThe reaction mixture was filtered
  3. customevaporated

Sources & evidence

ORD record
ord-a4a819e811f5431c9a5d59f502e9d230
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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