Water → 3-(4-Chloro-benzenesulfonyl)-3-(2,3,6-trifluoro-phenyl)-propan-1-ol

HRID 564301Notes

Reaction equation

HRID 564301 reaction equation
C([Si]([O:8][CH2:9][CH2:10][CH:11]([S:21]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)(=[O:23])=[O:22])[C:12]1[C:17]([F:18])=[CH:16][CH:15]=[C:14]([F:19])[C:13]=1[F:20])(C)C)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.O>C1COCC1>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([S:21]([CH:11]([C:12]2[C:17]([F:18])=[CH:16][CH:15]=[C:14]([F:19])[C:13]=2[F:20])[CH2:10][CH2:9][OH:8])(=[O:22])=[O:23])=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 58950531tert-Butyl-[3-(4-chloro-benzenesulfonyl)-3-(2,3,6-trifluoro-phenyl)-propoxy]-dimethyl-silane

Product 1

HCID 589505083-(4-Chloro-benzenesulfonyl)-3-(2,3,6-trifluoro-phenyl)-propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tert-butyl-[3-(4-chloro-benzenesulfonyl)-3-(2,3,6-trifluoro-phenyl)-propoxy]-dimethyl-silane (2.62 g, 5.47 mmol) was dissolved in 80 mL of THF and tetrabutylammonium fluoride (1.96 g, 7.51 mmol) was added at room temperature. The solution was stirred at room temperature overnight. 200 mL of EtOAc and 200 mL of water were added and the organic layer was separated. The organic layer was dried over Na2SO4 and concentrated. The product was purified by column chromatography using hex./EtOAc as the eluent (gradient from 0/100 to 75/25 in 45 min, 1.38 g, 69%). 1H NMR (CDCl3 400 MHz) δ 7.63 (d, J=8.8 Hz, 2H), 7.45 (d, J=8.8 Hz, 2H), 7.12 (m, 1H), 6.82 (m, 0.5H), 6.71 (m, 0.5H), 4.91 (m, 1H), 3.89 (m, 1H), 4.44 (m, 1H), 2.60 (m, 2H).

Workup

  1. customthe organic layer was separated
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe product was purified by column chromatography
  5. customas the eluent (gradient from 0/100 to 75/25 in 45 min, 1.38 g, 69%)

Sources & evidence

ORD record
ord-89a639f24e4342f6a696067456b2b124
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

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