Iodine → 2-Benzyloxy-4,6-dimethylpyridin-3-yl 4-methoxyphenyl methanol

HRID 916578Notes

Reaction equation

HRID 916578 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Mg].II.[CH2:13]([O:20][C:21]1[C:26]([CH:27]=[O:28])=[C:25]([CH3:29])[CH:24]=[C:23]([CH3:30])[N:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:13]([O:20][C:21]1[C:26]([CH:27]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)[OH:28])=[C:25]([CH3:29])[CH:24]=[C:23]([CH3:30])[N:22]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 5

HCID 807IodineHCID 77304-BromoanisoleHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 229349822-(Benzyloxy)-4,6-dimethylnicotinaldehyde

Product 1

HCID 694228852-Benzyloxy-4,6-dimethylpyridin-3-yl 4-methoxyphenyl methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A Grignard reagent (0.5 mol/L solution in tetrahydrofuran) was prepared in the usual way from 4-bromoanisole, magnesium, a catalytic amount of iodine and tetrahydrofuran. The obtained Grignard reagent (0.41 mL) was added to a solution of 2-benzyloxy-3-formyl-4,6-dimethylpyridine (0.019 g) in tetrahydrofuran (0.8 mL), and the mixture was stirred for 80 minutes at room temperature. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography on silica gel (developing solvent: hexane/ethyl acetate=4/1) to give 2-benzyloxy-4,6-dimethylpyridin-3-yl 4-Methoxyphenyl methanol (0.014 g) To a solution of the obtained 2-benzyloxy-4,6-dimethylpyridin-3-yl 4-methoxyphenyl methanol (0.014 g) in ethanol (1 mL) was added a catalytic amount of 10% palladium carbon powder, and the mixture was stirred for 2 hours at room temperature under a hydrogen atmosphere. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography on silica gel (developing solvent: dichloromethane/methanol=10/1) to give 3-(4-methoxybenzyl)-4,6-dimethyl-1H-pyridin-2-one (0.010 g).

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by preparative thin layer chromatography on silica gel (developing solvent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-d29f93970b6b443e9fca01e903824518
Source dataset
uspto-grants-2007_09
Patent number
US07271153B2

Reaction notes

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