HCID 18956332, 화합물 → HCID 18956329, 화합물

HRID 2379899노트

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HRID 2379899 반응식
[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]

참가 물질

4

반응물 2

HCID 18956332HCID 18956332, 화합물HCID 21226445Aluminium lithium hydride

생성물 1

HCID 18956329HCID 18956329, 화합물수율 84%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-5f793ef5eb294aa59b402e6614abef7b
출처 데이터셋
uspto-grants-1994_11
특허 번호
US05364875

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