2-Benzyloxy-4,6-dimethylpyridin-3-yl 4-(2-methoxymethyloxyethyl)phenyl methanol → 3-[4-(2-methoxymethyloxy-ethyl)benzyl]-4,6-dimethyl-1H-pyridin-2-one

HRID 916580ノート

反応式

HRID 916580 の反応式
C([O:8][C:9]1[C:14]([CH:15]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][O:25][CH2:26][O:27][CH3:28])=[CH:19][CH:18]=2)O)=[C:13]([CH3:29])[CH:12]=[C:11]([CH3:30])[N:10]=1)C1C=CC=CC=1>C(O)C.[C].[Pd]>[CH3:28][O:27][CH2:26][O:25][CH2:24][CH2:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:15][C:14]2[C:9](=[O:8])[NH:10][C:11]([CH3:30])=[CH:12][C:13]=2[CH3:29])=[CH:18][CH:19]=1

参加物

4

反応物 1

HCID 694217802-Benzyloxy-4,6-dimethylpyridin-3-yl 4-(2-methoxymethyloxyethyl)phenyl methanol

生成物 1

HCID 694233393-[4-(2-methoxymethyloxy-ethyl)benzyl]-4,6-dimethyl-1H-pyridin-2-one収率 91%

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 702Ethanol溶媒

実験手順

To a solution of 4-(2-methoxymethyloxyethyl) bromobenzene (0.60 g) in tetrahydrofuran (6 mL) was added tert-butyllithium (1.5 mol/L solution in hexane, 2.0 mL) at −78° C. under an argon atmosphere, and the mixture was stirred for 30 minutes. Then, a solution of 2-benzyloxy-3-formyl-4,6-dimethylpyridine (0.49 g) in tetrahydrofuran (5 mL) was added to the reaction mixture, and the mixture was stirred for 3 hours at 0° C. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with dimethyl ether. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1) to give 2-benzyloxy-4,6-dimethylpyridin-3-yl 4-(2-methoxymethyloxyethyl)phenyl methanol (0.74 g). To a solution of the obtained 2-benzyloxy-4,6-dimethylpyridin-3-yl 4-(2-methoxymethyloxyethyl)phenyl methanol (0.11 g) in ethanol (5.3 mL) was added 10% palladium carbon powder (0.065 g), and the mixture was stirred for 11 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: dichloro-methane/methanol=10/1) to give 3-[4-(2-methoxymethyloxy-ethyl)benzyl]-4,6-dimethyl-1H-pyridin-2-one (0.074 g).

後処理

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by preparative thin layer chromatography on silica gel (developing solvent: dichloro-methane/methanol=10/1)

出典と根拠

ORDレコード
ord-71ab7f429dd24a508c7ce3aa7f0cb3b5
出典データセット
uspto-grants-2007_09
特許番号
US07271153B2

反応ノート

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