Tetrahydrofuran → HCID 14790773, compound

HRID 1058289Notes

Reaction equation

HRID 1058289 reaction equation
O=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]1[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].C[Si](C)(C)[C:16]([F:19])([F:18])[F:17].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1C[O:43]CC1>Cl>[C:3]1([C:8]([OH:43])([C:16]([F:19])([F:18])[F:17])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 69939217HCID 69939217, compound

Product 1

HCID 14790773HCID 14790773, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To stirred ethyl 2-oxo-phenylacetate (1.0 g, 5.6 mmol) under nitrogen atmosphere at ambient temperature was added trimethyl(trifluoromethyl)silane (1.0 mL, 6.73 mmol) and 1.0 TBAF in THF (6.2 mL, 6.2 mmol). This mixture was stirred at ambient temperature for 72 h. To the reaction was added 5N HCl solution (10 mL) and the mixture was stirred at ambient temperature for 18 h. The mixture was partitioned between Et2O and water. The Et2O layer was separated, dried over anhydrous Na2SO4, and filtered. Crude ethyl 2-phenyl-2-hydroxy-3,3,3-trifluoropropanoate was obtained as a yellow oil (0.9 g; HPLC RT=3.30 min, method A; 1H NMR, 400 MHz, CDCl3, 8.2 ppm (d, 1H), 7.78 ppm (m, 1H), 7.4 ppm (m, 3H), 4.4 ppm (m, 2H), 1.35 ppm (t, 3H)).

Workup

  1. stirringthe mixture was stirred at ambient temperature for 18 h
  2. customThe mixture was partitioned between Et2O and water
  3. customThe Et2O layer was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-cb665fa280b6468189df6e6c9f433843
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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