Acetic Anhydride → (1-Trityl-1H-imidazol-4-YL)methyl acetate

HRID 2289139Notes

Reaction equation

HRID 2289139 reaction equation
[C:1]1([C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]2[CH:12]=[C:11]([CH2:13][OH:14])[N:10]=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:27](OC(=O)C)(=[O:29])[CH3:28].CCOC(C)=O>N1C=CC=CC=1>[C:21]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:8]2[CH:12]=[C:11]([CH2:13][O:14][C:27](=[O:29])[CH3:28])[N:10]=[CH:9]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 382182[1-(triphenylmethyl)-1H-imidazol-4-yl]methanol

Product 1

HCID 10762461(1-Trityl-1H-imidazol-4-YL)methyl acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Alcohol 2 (prepared above) was suspended in 500 mL of pyridine. Acetic anhydride (74 mL) was added dropwise, and the reaction was stirred for 48 hours during which it became homogeneous. The solution was poured into 2 L of EtOAc, washed with water (3×1 L), 5% aq. HCl soln. (2×1 L), sat. aq. NaHCO3, and brine, then dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product. The acetate 3 was isolated as a white powder (85.8 g) which was sufficiently pure for use in the next step.

Workup

  1. washwashed with water (3×1 L), 5% aq. HCl soln
  2. dry with material(2×1 L), sat. aq. NaHCO3, and brine, then dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide the crude product

Sources & evidence

ORD record
ord-42ff81219d564fc9af87512d5efd2219
Source dataset
uspto-grants-2000_07
Patent number
US06090948

Reaction notes

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