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

HRID 1698593Notes

Reaction equation

[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

Participants

Conditions

Temperature: 55 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-fb001b113a6e4fd499fd55d8d436e859
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163935B2

Reaction notes

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