Aluminium lithium hydride → 1-Trityl-1H-benzimidazol-5-yl-methanol

HRID 1815440

반응식

HRID 1815440 반응식
C[O:2][C:3]([C:5]1[CH:32]=[CH:31][C:8]2[N:9]([C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]=[N:11][C:7]=2[CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:12]([N:9]1[C:8]2[CH:31]=[CH:32][C:5]([CH2:3][OH:2])=[CH:6][C:7]=2[N:11]=[CH:10]1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 22710354methyl N-triphenylmethyl-5-benzimidazolecarboxylate

생성물 1

HCID 230215391-Trityl-1H-benzimidazol-5-yl-methanol수율 86.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To an ice-cooled stirred suspension of the product of step b (3.61 g, 7.94 mmol) in THF (30 ml) was added dropwise a solution of lithium aluminium hydride (1.0M in THF, 10 ml, 10.0 mmol). The suspension was stirred at this temperature for 1 h and then was quenched with saturated aqueous ammonium chloride (100 ml). The aqueous solution was extracted thrice with ethyl acetate (100 ml) and the combined organic phases were washed with brine (200 ml). The organic phase was dried over magnesium sulfate and the filtrate was evaporated at reduced pressure and the residue recrystallised from ethyl acetate/hexane to afford the title compound (2.68 g, 79%). 1H NMR 7.89 (1H, s), 7.74 (1H, d, 8.4), 7.33-7.17 (17H, m), 6.44 (1H, d, 0.9), 4.45 (2H, d, 6), 1.37 (1H, t, 6).

후처리

  1. stirringThe suspension was stirred at this temperature for 1 h
  2. customwas quenched with saturated aqueous ammonium chloride (100 ml)
  3. extractionThe aqueous solution was extracted thrice with ethyl acetate (100 ml)
  4. washthe combined organic phases were washed with brine (200 ml)
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. customthe filtrate was evaporated at reduced pressure
  7. customthe residue recrystallised from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-f7028a4a76bc44408a4da8a12b785a80
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06878736B1

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