2,2,2-Trifluoroethanol → HCID 86754668, compound

HRID 1741510Notes

Reaction equation

HRID 1741510 reaction equation
[F:1][CH:2]1[C:7]([Si](C)(C)C)=[C:6]([F:12])[CH:5]=[C:4]([S:13][CH3:14])[C:3]1([CH2:16][O:17][CH3:18])[OH:15].C(O)C(F)(F)F.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:1][CH:2]1[CH:7]=[C:6]([F:12])[CH:5]=[C:4]([S:13][CH3:14])[C:3]1([CH2:16][O:17][CH3:18])[OH:15]

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 2724141Tetrabutylammonium FluorideHCID 70247106HCID 70247106, compound

Product 1

HCID 86754668HCID 86754668, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A reaction mixture containing the trimethylsilyl derivative (28, 0.51 g, 1.74 mmol) in 10 mL of freshly distilled THF was treated with trifluoroethanol (0.18 g, 1.82 mmol) and tetrabutylammonium fluoride (1 M solution in THF, 1.74 mL, 1.74 mmol) at -78° C. under argon (FIG. 2E). The reaction mixture was allowed to stir at -78° C. for 20 min and at room temperature for 30 minutes. The reaction was quenched by the addition of water, followed by extraction with ethyl ether (2×15 mL). The combined organic extracts were washed with water, dried (MgSO4), filtered, and the solvent removed under vacuo. Silica gel chromatography (5% EtOAc:hexanes) gave the pure product as a colorless oil (270 mg, 71%). 1H NMR (CDCl3) δ 6.6-6.64 (m, 2H, ArH), 5.11 (s, 2H, CH2), 3.63 (s, 3H, CH3), 2.42 (s, 3H, CH3).

Workup

  1. customThe reaction was quenched by the addition of water
  2. extractionfollowed by extraction with ethyl ether (2×15 mL)
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed under vacuo

Sources & evidence

ORD record
ord-e70bcd70c75143f29759b0f169165621
Source dataset
uspto-grants-1999_10
Patent number
US05973191

Reaction notes

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