Sodium hydride → 1-(benzyloxymethyl)-2-phenyl-1H-imidazole

HRID 2104955Notes

Reaction equation

[C:1]1([C:7]2[NH:8][CH:9]=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:14](Cl)[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1.CCOC(C)=O>[CH2:16]([O:15][CH2:14][N:11]1[CH:10]=[CH:9][N:8]=[C:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To 2-phenylimidazole (500 mg, 3.47 mmol) in 10 mL THF at 0° C., was added 60% NaH (146 mg, 3.64 mmol). The mixture was stirred at 0° C. for 15 min, then BOM-Cl (80%, 656 μL, 3.82 mmol) was added. The mixture was stirred at rt for 1 h, then was diluted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 100% EtOAc/hexanes gradient) to afford 630 mg of Intermediate 15.1 as a colorless oil.

Workup

stirringThe mixture was stirred at rt for 1 h
washThe organic phase was washed with H2O and brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe crude product was purified by flash chromatography (0 to 100% EtOAc/hexanes gradient)

Sources & evidence

ORD record: ord-a810e054659449018fcd3067ca44f2a3
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576098B2

Reaction notes

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