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Diisobutylaluminumhydride → [2-(3-Methoxypropyl)-1-(2-trimethylsilanylethoxymethyl)-1H-benzoimidazol-4-yl]methanol

HRID 1176545
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HRID 1176545 반응식
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][O:12][CH2:13][CH2:14][CH2:15][C:16]1[N:20]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:19]2[CH:29]=[CH:30][CH:31]=[C:32]([C:33](OC)=[O:34])[C:18]=2[N:17]=1>O1CCCC1>[CH3:11][O:12][CH2:13][CH2:14][CH2:15][C:16]1[N:20]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:26])([CH3:27])[CH3:28])[C:19]2[CH:29]=[CH:30][CH:31]=[C:32]([CH2:33][OH:34])[C:18]=2[N:17]=1
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참가 물질

4

반응물 2

HCID 21225700DiisobutylaluminumhydrideHCID 68502641Methyl 2-(3-methoxypropyl)-1-(2-trimethylsilanylethoxymethyl)-1H-benzoimidazole-4-carboxylate

생성물 1

HCID 68503680[2-(3-Methoxypropyl)-1-(2-trimethylsilanylethoxymethyl)-1H-benzoimidazol-4-yl]methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-10 °C

실험 절차

35 ml of diisobutylaluminium hydride (1.5M in toluene) are added dropwise at −70° C. to a solution of 4.95 g of methyl 2-(3-methoxypropyl)-1-(2-trimethylsilanylethoxymethyl)-1H-benzoimidazole-4-carboxylate in 200 ml of tetrahydrofuran. The reaction mixture is then stirred at −10° C. for 1 hour and subsequently partitioned between tert-butyl methyl ether and 2:1 water/1N potassium bisulphate solution—the organic phase is washed with saturated aqueous sodium bicarbonate solution and water, dried over sodium sulphate and concentrated by evaporation. The combined aqueous phases are reextracted with ethyl acetate (3×)—the combined organic phases are washed with saturated aqueous sodium bicarbonate solution and water, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow oil from the residues by means of flash chromatography (SiO2 60F). Rf=0.21 (95:5 ethyl acetate-methanol); Rt=3.91.

후처리

  1. customsubsequently partitioned between tert-butyl methyl ether and 2:1 water/1N potassium bisulphate solution—the organic phase
  2. washis washed with saturated aqueous sodium bicarbonate solution and water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation
  5. washare washed with saturated aqueous sodium bicarbonate solution and water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation

출처 및 근거

ORD 기록
ord-fc4d1b89c33f45a885cd14b23d8a19e4
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07842688B2

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