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

HRID 2306166Notes

Reaction equation

HRID 2306166 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]([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)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1.[C:27](OC(=O)C)(=[O:29])[CH3:28].CCOC(C)=O>N1C=CC=CC=1>[C:27]([O:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:7]=1)(=[O:29])[CH3:28]

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

4-(Hydroxymethyl)-1-(triphenylmethyl)imidazole, as described above in Step A, (88.5 g, 260 mmol) was suspended in pyridine (500 mL). Acetic anhydride (74 mL, 780 mmol) was added dropwise, and the reaction was stirred for 48 hours during which it became homogeneous. The solution was poured into EtOAc, and washed sequentially with water, 5% aqueous HCl solution, saturated aqueous NaHCO3 solution, and brine. The organic extracts were dried (Na2SO4), and concentrated in vacuo to provide the ester as a white powder.

Workup

  1. washwashed sequentially with water, 5% aqueous HCl solution, saturated aqueous NaHCO3 solution, and brine
  2. dry with materialThe organic extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-21ef851c59ec4153a636a6e124b917d8
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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