Tetrabutylammonium Fluoride → HCID 11661439, compound

HRID 1822133Notes

Reaction equation

HRID 1822133 reaction equation
[CH2:1]([N:3]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([O:28][Si](CC)(CC)CC)([C:24]([F:27])([F:26])[F:25])[C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)[CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:6])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([N:3]([CH2:4][CH:5]([OH:6])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:13]1[CH:14]=[CH:15][C:16]([C:19]([OH:28])([C:24]([F:25])([F:26])[F:27])[C:20]([F:23])([F:22])[F:21])=[CH:17][CH:18]=1)[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86602505HCID 86602505, compound

Product 1

HCID 11661439HCID 11661439, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 300 mg (0.58 mmol) of 2-{ethyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-phenyl]-amino}-1-phenyl-ethanol in 7.5 mL of THF was treated with 1.5 mL of a 1M TBAF-solution in THF and stirred at RT for 1 hour. Evaporation of the solvent and column chromatography on silica gel with n-heptane/EtOAc 9:1 yielded 153 mg (65%) of 2-{4-[ethyl-(2-hydroxy-2-phenyl-ethyl)-amino]-phenyl}-1,1,1,3,3,3-hexafluoro-propan-2-ol, white solid, MS: 408 (MH+).

Workup

  1. customEvaporation of the solvent and column chromatography on silica gel with n-heptane/EtOAc 9:1

Sources & evidence

ORD record
ord-a2065b67e120448987b94afdbe37854b
Source dataset
uspto-grants-2009_10
Patent number
US07608721B2

Reaction notes

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