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

HRID 1698593ノート

反応式

HRID 1698593 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
55 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fb001b113a6e4fd499fd55d8d436e859
出典データセット
uspto-grants-2012_04
特許番号
US08163935B2

反応ノート

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