Water → HCID 69691756, compound

HRID 1814320Notes

Reaction equation

HRID 1814320 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.[C:10]([OH:14])(C)([CH3:12])[CH3:11].[CH3:15]C(C)([O-])C.[K+].O>C1COCC1>[N:1]1([C@@H:11]([CH3:15])[C@@H:10]([CH3:12])[OH:14])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 5798BenzimidazoleHCID 6386tert-ButanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 69691756HCID 69691756, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

Benzimidazole (950 mg, 8.0 mmol) in THF was added to tert-butanol (20 mL) and THF (2.5 mL) containing potassium tert-butoxide (900 mg, 8.0 mmol). 2R,3R-butene oxide (500 mg, ˜1 equiv) was added. The reaction was heated in a sealed tube at 60° C. for 2 days. After cooling to room temperature, the reaction was poured into water, extracted with ethyl acetate, washed with 1.0N sodium hydroxide, then brine. To give (1R,2S)-2-benzimidazol-1-yl-1-methyl-propanol 1.27 g (84%) as a yellow oil. MS (APCI) m/z 191.2 (M+1).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with 1.0N sodium hydroxide

Sources & evidence

ORD record
ord-b13baee60004403196f900b92dbb8cb1
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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