Water → 4-(3-Acetoxy)propyl-2-fluoro-1-triphenylmethylimidazole

HRID 2412475Notes

Reaction equation

HRID 2412475 reaction equation
[F:1][C:2]1[N:3]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=[C:5]([CH2:7][CH2:8][CH2:9][OH:10])[N:6]=1.[C:30](Cl)(=[O:32])[CH3:31].O>N1C=CC=CC=1>[C:30]([O:10][CH2:9][CH2:8][CH2:7][C:5]1[N:6]=[C:2]([F:1])[N:3]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:4]=1)(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 204324552-Fluoro-4-(3-hydroxypropyl)-1-triphenylmethylimidazole

Product 1

HCID 204323374-(3-Acetoxy)propyl-2-fluoro-1-triphenylmethylimidazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-fluoro-4-(3-hydroxy)propyl-1-triphenylmethylimidazole (386 mg. in dry pyridine (2 ml.) and acetyl chloride (78.5 μl.) was heated with stirring at 85° for 100 minutes. The solution was poured into water (25 ml.) and the mixture extracted with CH2Cl2 (3×15 ml.). The extract was washed with water and brine, dried (MgSO4), filtered, evaporated, and the residue azeotroped with toluene. The resulting orange oil was purified by column chromatography on silica gel eluting with CH2Cl2 /MeOH 100:0 to 98:2 v/v to give 4-(3-acetoxy)propyl-2-fluoro-1-triphenylmethylimidazole (127 mg.) having the following n.m.r. in CDCl3 : 1.9 (m, 2H); 2.02 (s, 3H); 2.47 (t, 2H); 4.07 (t, 2H) 6.22 (s, 1H); 7.0-7.5 (m, 15H).

Workup

  1. extractionthe mixture extracted with CH2Cl2 (3×15 ml.)
  2. washThe extract was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customthe residue azeotroped with toluene
  7. customThe resulting orange oil was purified by column chromatography on silica gel eluting with CH2Cl2 /MeOH 100:0 to 98:2 v/v

Sources & evidence

ORD record
ord-8694bce57a264716abdcec65057b75ac
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

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