Acetic Acid → 4-(3-Pyridylmethyl)benzoic acid methyl ester

HRID 2296047Notes

Reaction equation

HRID 2296047 reaction equation
COC(=O)/C=C/C1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:8][CH:7]=1.[C-:20]#N.[Na+].[C:23]([OH:26])(=[O:25])[CH3:24]>[O-2].[O-2].[Mn+4].CO>[CH3:20][O:25][C:23](=[O:26])[C:24]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 12882181(E)-3-[4-(3-Pyridylmethyl)phenyl]acrylic acid methyl ester

Product 1

HCID 541209054-(3-Pyridylmethyl)benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of 300 mg of the aldehyde (prepared as described in Reference Example 1), 370 mg of sodium cyanide, 3.0 g of manganese dioxide, 0.18 ml of acetic acid and 15 ml of methanol was stirred overnight at room temperature, filtered through a pad of infusorial earth, and the filtrate was concentrated under reduced pressure. To the residue was added a saturated aqueous solution of sodium bicarbonate, and extracted with chloroform. The extract was washed with water, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (3:2) as eluent to give 255 mg of the title compound having the following physical characteristics:

Workup

  1. filtrationfiltered through a pad of infusorial earth
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the residue was added a saturated aqueous solution of sodium bicarbonate
  4. extractionextracted with chloroform
  5. washThe extract was washed with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel using
  9. additiona mixture of cyclohexane and ethyl acetate (3:2) as eluent

Sources & evidence

ORD record
ord-2ce796236a61429ebf663035d5be518c
Source dataset
uspto-grants-1984_01
Patent number
US04427682

Reaction notes

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