Methyl 4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoate → 4-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol

HRID 644005

反応式

HRID 644005 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:12][CH:11]=1>C1COCC1>[CH3:23][C:22]1[O:21][C:20]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[N:19][C:18]=1[CH2:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][OH:8])=[CH:15][CH:14]=1

参加物

4

反応物 2

HCID 11461459Methyl 4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 110228074-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

Lithium aluminum hydride (15.5 mL of a 1.0 M solution in THF) is added slowly to a cooled (ice-water bath) solution of the title B compound, 4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzoic acid methyl ester (2.0 g, 6.18 mmol) in THF (30 mL). The mixture is stirred at 0° C. for 3 h, then quenched with saturated sodium bicarbonate, and extracted with EtOAc. The organic solution is washed with brine, dried over magnesium sulfate, and concentrated under vacuum to give the crude product. The product is purified by silica gel chromatography using 30% EtOAc in hexane as the eluent to give [4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-methanol as a white solid.

後処理

  1. customquenched with saturated sodium bicarbonate
  2. extractionextracted with EtOAc
  3. washThe organic solution is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customto give the crude product
  7. customThe product is purified by silica gel chromatography

出典と根拠

ORDレコード
ord-b3bd0b1ad8524663a3d75ea4da848814
出典データセット
uspto-grants-2010_04
特許番号
US07700637B2

関連ノート

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