Water → (5-ethynyl-1-methyl-1H-imidazol-2-yl)-phenyl-methanol

HRID 2109212Notes

Reaction equation

HRID 2109212 reaction equation
[C:1]([C:3]1[N:7]([CH3:8])[C:6]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])=[N:5][CH:4]=1)#[CH:2].[BH4-].[Na+].O>CO>[C:1]([C:3]1[N:7]([CH3:8])[C:6]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[OH:10])=[N:5][CH:4]=1)#[CH:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 21097345(5-Ethynyl-1-methyl-1H-imidazol-2-yl)-phenyl-methanone

Product 1

HCID 21097344(5-ethynyl-1-methyl-1H-imidazol-2-yl)-phenyl-methanolYield 37.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 200 mg (0.951 mmol) of (5-ethynyl-1-methyl-1H-imidazol-2-yl)-phenyl-methanone in 1 mL of MeOH was added dropwise to a 0° C. solution of 54 mg (1.43 mmol) of NaBH4 in 5 mL of MeOH. After stirring for 2 h, 10 mL of water was added and the mixture was extracted with CH2Cl2 (3×50 mL). The combined extracts were washed with brine, dried with MgSO4, filtered, concentrated, and chromatographed (0-80% EtOAc in hexanes) to give (5-ethynyl-1-methyl-1H-imidazol-2-yl)-phenyl-methanol as a white solid (75 mg).

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (3×50 mL)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed (0-80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ee09141af51c46feb6c6664e2ac0f1c7
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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