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

HRID 2187869Notes

Reaction equation

HRID 2187869 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 hrs 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-e5cca7cc9f8d416e9245631bb3d316eb
Source dataset
uspto-grants-2002_06
Patent number
US06410534B1

Reaction notes

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