Lithium borohydride → [2-(2,4-Dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazol-4-yl]methanol

HRID 1698593노트

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HRID 1698593 반응식
[Cl:1][C:2]1[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([CH3:29])[C:3]=1[O:4][C:5]1[N:9]([CH3:10])[C:8]2[C:11]([CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:12][CH:13]=[C:14]([C:15](OC)=[O:16])[C:7]=2[N:6]=1.[BH4-].[Li+]>O1CCCC1>[Cl:1][C:2]1[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([CH3:29])[C:3]=1[O:4][C:5]1[N:9]([CH3:10])[C:8]2[C:11]([CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:12][CH:13]=[C:14]([CH2:15][OH:16])[C:7]=2[N:6]=1

참가 물질

4

반응물 2

HCID 4148881Lithium borohydrideHCID 58012435Methyl 2-(2,4-dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carboxylate

생성물 1

HCID 58012349[2-(2,4-Dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazol-4-yl]methanol수율 98.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
55 °C

실험 절차

A mixture of methyl 2-(2,4-dichloro-6-methylphenoxy)-7-(1-ethylpropyl)-1-methyl-1H-benzimidazole-4-carboxylate (1.00 g, 2.30 mmol), lithium borohydride (100 mg, 4.60 mmol) and tetrahydrofuran (20 ml) was heated at 55° C. for 1 h. The reaction mixture was concentrated in vacuo. The residue was diluted with aqueous saturated sodium bicarbonate and extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel with a 30% ethyl acetate/n-hexane to give 920 mg (2.26 mmol, 98%) of the title compound as a white powder.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe residue was diluted with aqueous saturated sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel with a 30% ethyl acetate/n-hexane

출처 및 근거

ORD 기록
ord-fb001b113a6e4fd499fd55d8d436e859
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163935B2

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