Sodium hydride → tert-Butyl 2-[4-(2-butyl-4-chloro-5-formyl-imidazol-1-yl-methyl)phenyl]-2-cyclopentylacetate

HRID 37219Notes

Reaction equation

[H-].[Na+].[CH2:3]([C:7]1[NH:8][C:9]([CH:13]=[O:14])=[C:10]([Cl:12])[N:11]=1)[CH2:4][CH2:5][CH3:6].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:19][CH:18]=1>CN(C=O)C>[CH2:3]([C:7]1[N:8]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([CH:23]([CH:31]3[CH2:32][CH2:33][CH2:34][CH2:35]3)[C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])=[CH:21][CH:22]=2)[C:9]([CH:13]=[O:14])=[C:10]([Cl:12])[N:11]=1)[CH2:4][CH2:5][CH3:6]

Participants

Conditions

Temperature: 0 °C

Procedure

1.6 g (0.053 mol) of sodium hydride (80%) are suspended under protective gas in 50 ml of DMF, 10 g (0.053 mol) of 2-butyl-5-formyl-4-chloroimidazole (preparation as described in EP 324,377) in 100 ml of DMF are added dropwise at 0° C., the mixture is subsequently stirred for 15 minutes at 0° C., and 18.9 g (0.053 mol) of tert-butyl 2-(4-bromomethylphenyl)-2-cyclopentyl-acetate in 100 ml of DMF are added dropwise. Stirring is continued for 2 hours at 0° C., the solvent is evaporated, the residue is taken up in diethyl ether, the mixture is filtered, and the product is concentrated and then chromatographed over silica gel 60 using dichloromethane. Yield: 16.2 g (66.7% of theory)

Workup

stirringStirring
waitis continued for 2 hours at 0° C.
customthe solvent is evaporated
filtrationthe mixture is filtered
concentrationthe product is concentrated
customchromatographed over silica gel 60 using dichloromethane

Sources & evidence

ORD record: ord-bbf55e86722a4393af6e6479b9f83698
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420149

Reaction notes

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