HCID 18956332、化合物 → HCID 18956329、化合物

HRID 2379899ノート

反応式

HRID 2379899 の反応式
[C:1]([CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[CH:19]([CH3:21])[CH3:20])(OCC)=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:2][CH2:1][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[CH:19]([CH3:21])[CH3:20]

参加物

4

反応物 2

HCID 18956332HCID 18956332、化合物HCID 21226445Aluminium lithium hydride

生成物 1

HCID 18956329HCID 18956329、化合物収率 84%

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

Part B. A solution of the ester obtained in Part A above (9.54 g, 33.1 mmol) in tetrahydrofuran (30 mL) was added to a solution of lithium aluminum hydride (80 mmol) in tetrahydrofuran (80 mL) at 0° C. The mixture was heated to reflux overnight, then cooled back to 0° C. and quenched by the careful sequential addition of water (3 mL), then aqueous sodium hydroxide solution (10 mL of 15%), then water (10 mL). The mixture was filtered through celite with copius tetrahydrofuran washing, and the liquid was dried over anhydrous potassium carbonate, filtered and evaporated. The residual oil was separated by flash chromatography (ethyl acetate) to afford the product, 1-(5-hydroxypentyl)-2-(1-methylethyl)-1H-benzimidazole (6.82 g, 27.7 mmol, 84%) as an oil. 1H NMR (CDCl3) : 7.78-7.70 (1H, m); 7.32-7.22 (3H, m); 4.90 (1H, br d, J=2.2 Hz); 4.12 (2H, t, J=7.5 Hz); 3.64 (2H, t, J=6.0 Hz); 3.18 (1H, m, J=6.6 Hz); 1.93-1.45 (6H, m); 1.44 (6H, d, J=6.6 Hz).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customquenched by the careful sequential addition of water (3 mL)
  4. filtrationThe mixture was filtered through celite with copius tetrahydrofuran washing
  5. dry with materialthe liquid was dried over anhydrous potassium carbonate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residual oil was separated by flash chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-5f793ef5eb294aa59b402e6614abef7b
出典データセット
uspto-grants-1994_11
特許番号
US05364875

反応ノート

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