Water → 5-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyrazine-2-carboxylic acid methyl ester

HRID 1435828ノート

反応式

HRID 1435828 の反応式
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][OH:14].[H-].[Na+].Cl[C:18]1[N:19]=[CH:20][C:21]([C:24]([O:26][CH3:27])=[O:25])=[N:22][CH:23]=1.O>C1COCC1>[CH3:27][O:26][C:24]([C:21]1[CH:20]=[N:19][C:18]([O:14][CH2:13][C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:5][O:6][C:2]=2[CH3:1])=[CH:23][N:22]=1)=[O:25]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 406081Methyl 5-chloropyrazine-2-carboxylateHCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanol

生成物 1

HCID 426360595-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyrazine-2-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (5-methyl-3-phenyl-isoxazol-4-yl)-methanol (1.24 g, 6.55 mmol) in THF (12 mL) was added sodium hydride (55% dispersion in mineral oil, 0.31 g, 7.2 mmol) at 0° C. The reaction mixture was stirred for 30 min while it was allowed to warm up to room temperature. Methyl 5-chloropyrazine-2-carboxylate (1.36 g, 7.86 mmol) was added and stirring was continued for 2 h. Water (10 mL) was added and the mixture was extracted with ethyl acetate (40 mL). The combined organic layers were washed with brine (10 mL) and dried over sodium sulfate. Concentration and purification of the residue by chromatography (SiO2, heptane:ethyl acetate=80:20 to 50:50, 1.00 g, 47%) which was obtained as a light yellow oil. MS: m/e=326.2 [M+H]+.

後処理

  1. stirringstirring
  2. waitwas continued for 2 h
  3. extractionthe mixture was extracted with ethyl acetate (40 mL)
  4. washThe combined organic layers were washed with brine (10 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationConcentration and purification of the residue by chromatography (SiO2, heptane:ethyl acetate=80:20 to 50:50, 1.00 g, 47%) which
  7. customwas obtained as a light yellow oil

出典と根拠

ORDレコード
ord-f1913e7cbef34068ac984194ac575796
出典データセット
uspto-grants-2009_11
特許番号
US07618973B2

反応ノート

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