Tetrabutylammonium Fluoride → HCID 58629884, compound

HRID 1391798Notes

Reaction equation

HRID 1391798 reaction equation
CC([Si](C)(C)[O:6][CH2:7][CH:8]([O:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:28]([CH3:39])[CH:27]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[N:10]=1)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:6][CH2:7][CH:8]([O:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:28]([CH3:39])[CH:27]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:23])([F:22])[F:24])=[CH:19][CH:20]=2)[N:10]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58629929HCID 58629929, compound

Product 1

HCID 58629884HCID 58629884, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl ({4-[(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}ethyl)oxy]-2-methylphenyl}oxy)acetate (208 mg, 0.352 mmol) in THF (3.5 mL) was added TBAF (1M in THF, 0.458 mL) dropwise over 1 min. The resulting solution was then stirred at ambient temperature for 18 h. The mixture was then reduced under vacuum and the residue purified by SPE (silica, 10 g cartridge) eluting with cyclohexane:EtOAc (gradient 15:1 to 2:1) to afford the title compound (89 mg).

Workup

  1. customthe residue purified by SPE (silica, 10 g cartridge)
  2. washeluting with cyclohexane

Sources & evidence

ORD record
ord-a2dc540763fe4b77b79326bbd4b99aed
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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