Tetrabutylammonium Fluoride → HCID 178487495, compound

HRID 1368532Notes

Reaction equation

HRID 1368532 reaction equation
[Si]([O:8][CH:9]([C:11]1[C:20]([O:21][CH3:22])=[CH:19][CH:18]=[C:17]2[C:12]=1[CH:13]=[CH:14][C:15]([C:23]([C:28]1[N:29]=[CH:30][NH:31][CH:32]=1)([OH:27])[CH:24]([CH3:26])[CH3:25])=[CH:16]2)[CH3:10])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][CH:9]([C:11]1[C:20]([O:21][CH3:22])=[CH:19][CH:18]=[C:17]2[C:12]=1[CH:13]=[CH:14][C:15]([C:23]([C:28]1[N:29]=[CH:30][NH:31][CH:32]=1)([OH:27])[CH:24]([CH3:26])[CH3:25])=[CH:16]2)[CH3:10]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178487496HCID 178487496, compound

Product 1

HCID 178487495HCID 178487495, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

1-[5-[1-(tert-Butyldimethylsilyloxy)ethyl]-6-methoxynaphthalen-2-yl]-1-(1H-imidazol-4-yl)-2-methyl-1-propanol (0.499 g) was dissolved in THF (5 ml). To the solution was added tetrabutylammonium fluoride (1.0M in THF; 5 ml), and the mixture was stirred at 60° C. for 8 h. The reaction mixture was concentrated. The obtained residue was purified by silica gel column chromatography (eluent, ethyl acetate:methanol=1:0→10:1) and washed with hexane to give the titled compound (0.24 g) as an amorphous product.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe obtained residue was purified by silica gel column chromatography (eluent, ethyl acetate:methanol=1:0→10:1)
  3. washwashed with hexane

Sources & evidence

ORD record
ord-0071f4c874c74c9c8cacbe6c31d29a1f
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

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