Water → (1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methanol

HRID 475173ノート

反応式

HRID 475173 の反応式
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16](OC)=[O:17])=[CH:15][C:10]=2[N:9]=[CH:8]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH2:16][OH:17])=[CH:15][C:10]=2[N:9]=[CH:8]1

参加物

6

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 58324962methyl 1-(tetrahydro-2H-pyran-2-yl)-1H-benzimidazole-5-carboxylate

生成物 1

HCID 58325018(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methanol収率 100.3%

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

A solution of 22 (2.5 g, 9.61 mmol) in anhydrous THF (10 mL) was added dropwise to a mixture of LiAlH4 (0.55 g, 14.42 mmol) in anhydrous THF (20 mL) at 0° C. under nitrogen. The reaction mixture was stirred for 30 min at 0° C. then treated sequentially with water (2 mL) and 10% NaOH (1.8 mL). The resulting mixture was extracted with ether (2×100 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to afford 2.24 g (95%) of (1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methanol (24) as yellow oil: MS (ESI) m/z=233.2 [M+1]+.

後処理

  1. extractionThe resulting mixture was extracted with ether (2×100 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-b105b8d8ad87430ca0e5f137e1fd7d4c
出典データセット
uspto-grants-2014_01
特許番号
US08637537B2

反応ノート

読み込み中…