Water → 2-(2-Phenyl-4-thiazolylmethoxy)-5-pyridylmethanol

HRID 349974

反応式

HRID 349974 の反応式
[H-].[Na+].[C:3]1([C:9]2[S:10][CH:11]=[C:12]([CH2:14][OH:15])[N:13]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:17]1[N:22]=[CH:21][C:20]([C:23](OC)=[O:24])=[CH:19][CH:18]=1.O>CN(C)C=O>[C:3]1([C:9]2[S:10][CH:11]=[C:12]([CH2:14][O:15][C:17]3[N:22]=[CH:21][C:20]([CH2:23][OH:24])=[CH:19][CH:18]=3)[N:13]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 27764734-(Hydroxymethyl)-2-phenyl-1,3-thiazole

生成物 1

HCID 229307412-(2-Phenyl-4-thiazolylmethoxy)-5-pyridylmethanol収率 56%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (60%, oily, 1.40 g) was added to a solution of 2-phenyl-4-thiazolylmethanol (6.69 g) and methyl 6-chloro-3-pyridinecarboxylate (6.01 g) in N,N-dimethylformamide (100 ml) at 0° C., and the mixture was stirred for 30 minutes. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. Lithium aluminium hydride (1.33 g) was added to a solution of the residue in tetrahydrofuran (150 ml) at 0° C., which was stirred at room temperature for 10 minutes. Sodium sulfate decahydrate (11.3 g) was added to the reaction mixture, which was stirred for 30 minutes at room temperature. The precipitate was removed by filtration, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography to obtain 6-(2-phenyl-4-thiazolylmethoxy)-3-pyridylmethanol (5.81 g, yield 56%) as colorless crystals from the fraction eluted with tetrahydrofuran. This was recrystallized from tetrahydrofuran-hexane. Melting point: 134–135° C.

後処理

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. additionLithium aluminium hydride (1.33 g) was added to a solution of the residue in tetrahydrofuran (150 ml) at 0° C.
  6. stirringwhich was stirred at room temperature for 10 minutes
  7. additionSodium sulfate decahydrate (11.3 g) was added to the reaction mixture, which
  8. stirringwas stirred for 30 minutes at room temperature
  9. customThe precipitate was removed by filtration
  10. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-fe6f88ac39404eb3ac419da1680916c0
出典データセット
uspto-grants-2007_02
特許番号
US07179823B1

関連ノート

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