(6-tert-Butyldimethylsilyloxy-2-naphthyl)(1-trityl-1H-imidazol-4-yl)methanol → (6-tert-Butyldimethylsilyloxy-2-naphthyl)(1-trityl-1H-imidazol-4-yl)methanone

HRID 480448Notes

Reaction equation

HRID 480448 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([CH:19]([C:21]1[N:22]=[CH:23][N:24]([C:26]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:25]=1)[OH:20])[CH:13]=[CH:12]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>ClCCl.O=[Mn]=O>[Si:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]([C:21]1[N:22]=[CH:23][N:24]([C:26]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH:25]=1)=[O:20])[CH:13]=[CH:12]2)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 18769033(6-tert-Butyldimethylsilyloxy-2-naphthyl)(1-trityl-1H-imidazol-4-yl)methanol

Product 1

HCID 18769054(6-tert-Butyldimethylsilyloxy-2-naphthyl)(1-trityl-1H-imidazol-4-yl)methanoneYield 92.8%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (6-tert-butyldimethylsilyloxy-2-naphthyl)(1-trityl-1H-imidazol-4-yl)methanol (49.0 g) in dichloromethane (400 mL) was added MnO2 (150 g) and the mixture was stirred for 3 h at room temperature. The reaction mixture was filtered and the filtrate was concentrated to give the titled compound (45.3 g) as a pale yellow powder.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c75ad8a8dc244fe7a7ad4b21a5cf47ee
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

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