1-(triphenylmethyl)-1H-imidazole-4-carbaldehyde → 1-(1-trityl-1H-imidazol-4-yl)ethanol

HRID 2074108Notes

Reaction equation

HRID 2074108 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([CH:25]=[O:26])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][Mg]Br>C1COCC1>[C:1]([N:20]1[CH:24]=[C:23]([CH:25]([OH:26])[CH3:27])[N:22]=[CH:21]1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 123447941-(1-trityl-1H-imidazol-4-yl)ethanolYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-trityl-1H-imidazole-4-carbaldehyde (10.0 g, 0.03 mol) in anhydrous THF (100 mL) was added dropwise methyl magnesium bromide (1.4 M in hexane, 52.8 mL, 0.075 mol) at 0° C. After the addition, the mixture was stirred at RT overnight. The reaction was quenched with sat. aq. NH4Cl (50 mL) and the mixture extracted with CH2Cl2 (3×50 mL). The organic layers were combined, washed with 1 N aq. NaOH (3×20 mL), water (3×20 mL) and brine (100 mL), dried over MgSO4 and evaporated. The residue was purified via column chromatography (silica gel, EtOAc/Petroleum ether 1:5) to yield the title compound (8.0 g, 75.0%) as a white solid.

Workup

  1. additionAfter the addition
  2. customThe reaction was quenched with sat. aq. NH4Cl (50 mL)
  3. extractionthe mixture extracted with CH2Cl2 (3×50 mL)
  4. washwashed with 1 N aq. NaOH (3×20 mL), water (3×20 mL) and brine (100 mL)
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe residue was purified via column chromatography (silica gel, EtOAc/Petroleum ether 1:5)

Sources & evidence

ORD record
ord-c2815767cb224e449d20893ad90ffaff
Source dataset
uspto-grants-2011_04
Patent number
US07919488B2

Reaction notes

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