Acetone → 4-(2,3-Dihydroxypropyl)-2-fluoro-1-triphenylmethylimidazole

HRID 2412506Notes

Reaction equation

HRID 2412506 reaction equation
CN1CC[O:5]CC1.C([C:11]1[N:12]=[C:13]([F:35])[N:14]([C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=1)C=C.[CH3:36][C:37]([CH3:39])=[O:38]>[Os](=O)(=O)(=O)=O>[OH:38][CH:37]([CH2:39][OH:5])[CH2:36][C:11]1[N:12]=[C:13]([F:35])[N:14]([C:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 180Acetone2×HCID 79724-MethylmorpholineHCID 204323494-Allyl-2-fluoro-1-triphenylmethylimidazole

Product 1

HCID 204323234-(2,3-Dihydroxypropyl)-2-fluoro-1-triphenylmethylimidazole

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

A solution of osmium tetroxide in acetone was treated with N-methylmorpholine in aqueous acetone. 4-Allyl-2-fluoro-1-triphenylmethylimidazole was added, and the mixture stirred at ambient temperature overnight. Reductive work-up with sodium metabisulphite and magnesium trisilicate, followed by extraction into ether, gave 4-(2,3-dihydroxypropyl)-2-fluoro-1-triphenylmethylimidazole, having the following n.m.r. in CDCl3 : 2.6 (d, 2H); 3.6 (m, 2H); 3.9 (m, 1H); 6.3 (s, 1H); 7.0-7.5 (m, 15H).

Workup

  1. extractionReductive work-up with sodium metabisulphite and magnesium trisilicate, followed by extraction into ether

Sources & evidence

ORD record
ord-3c708071408c425f843efec8bd266875
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

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