Tetrabutylammonium Fluoride → 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthol

HRID 1061870Notes

Reaction equation

[Si]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]([C:24]1[N:25]=[CH:26][N:27]([C:29]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:28]=1)([OH:23])[CH:20]([CH3:22])[CH3:21])[CH:13]=[CH:12]2)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:23][C:19]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([OH:8])[CH:18]=[CH:17]2)([C:24]1[N:25]=[CH:26][N:27]([C:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:28]=1)[CH:20]([CH3:21])[CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

1-(6-tert-Butyldimethylsilyloxy-2-naphthyl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (35.0 g) was dissolved in THF (100 mL) and cooled to 0° C. A solution (1 M: 100 mL) of tetrabutylammonium fluoride in THF was added dropwise. The mixture was stirred at room temperature for 1 hr., and the solvent was evaporated and water was added to the residue. The resulting precipitate was collected by filtration, washed with ether and water and dried to give the title compound (28.3 g) as a colorless powder.

Workup

custom, and the solvent was evaporated
additionwater was added to the residue
filtrationThe resulting precipitate was collected by filtration
washwashed with ether and water
customdried

Sources & evidence

ORD record: ord-f1ab5871e07143e3888a53eb3d5ce653
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06960586B2

Reaction notes

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