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

HRID 399135Notes

Reaction equation

HRID 399135 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

1-Triphenylmethyl-4-(hydroxymethyl)-imidazole (260 mmol) was suspended in pyridine (500 mL). Acetic anhydride (74 mL, 780 mmol) was added dropwise, and the reaction was stirred for 48 hr during which it became homogeneous. The solution was poured into EtOAc, washed sequentially with water, 5% aqueous HCl solution, satd aqueous NaHCO3, solution, and brine. The organic extracts were dried (Na2SO4), and concentrated in vacuo to provide the product as a white powder, which was sufficiently pure for use in the next reaction.

Workup

  1. washwashed sequentially with water, 5% aqueous HCl solution
  2. dry with materialThe organic extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3add961944cc4fe99646873fa67f031c
Source dataset
uspto-grants-1998_10
Patent number
US05817678

Reaction notes

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