Water → HCID 178519336, compound

HRID 1243802Notes

Reaction equation

HRID 1243802 reaction equation
C[O:2][C:3]([C:5]1[CH:19]=[CH:18][C:8]2[NH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:11][C:7]=2[CH:6]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[C:12]1([C:10]2[NH:9][C:8]3[CH:18]=[CH:19][C:5]([CH2:3][OH:2])=[CH:6][C:7]=3[N:11]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178497340HCID 178497340, compound

Product 1

HCID 178519336HCID 178519336, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-Phenyl-1H-benzoimidazole-5-carboxylic acid methyl ester (1.178 g, 4.67 mmol) was dissolved in 20 mL THF. Cooled to 0° C. and then added LAH (886 mg, 23.35 mmol). The mixture was heated to 50° C. overnight. Added 0.9 mL water, 0.9 mL 15% NaOH aqu. solution then 3 mL water. Stirred at RT for 30 mins. Filtered through celite and washed the celite with ethyl acetate. Washed the filtrate with brine. Dried over Na2SO4. Filtered and removed solvent in vacuo. Obtained 783 mg (74.8%) of (2-Phenyl-1H-benzoimidazol-5-yl)-methanol as an off white foam.

Workup

  1. temperatureThe mixture was heated to 50° C. overnight
  2. filtrationFiltered through celite
  3. washwashed the celite with ethyl acetate
  4. washWashed the filtrate with brine
  5. dry with materialDried over Na2SO4
  6. filtrationFiltered
  7. customremoved solvent in vacuo

Sources & evidence

ORD record
ord-d7458f8f8efc43b8a9a2d903442f0b95
Source dataset
uspto-grants-2006_10
Patent number
US07119102B2

Reaction notes

Loading…