4-Methoxybenzyl alcohol → (R)-1,1,1-Trifluoro-3-[(4-methoxybenzyl)oxy]-2-propanol

HRID 420317Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 420317
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1.[CH2:13]1[O:15][C@H:14]1[C:16]([F:19])([F:18])[F:17]>C1COCC1.O>[F:17][C:16]([F:19])([F:18])[C@H:14]([OH:15])[CH2:13][O:10][CH2:9][C:8]1[CH:11]=[CH:12][C:5]([O:4][CH3:3])=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 7016923(2R)-2-(trifluoromethyl)oxirane

Produkt 1

HCID 66649618(R)-1,1,1-Trifluoro-3-[(4-methoxybenzyl)oxy]-2-propanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of NaH (390 mg, 8.9 mmol, 55% in mineral oil) in THF (10 mL) at 0° C. was added 4-methoxybenzylalcohol (1.27 g, 8.92 mmol) in THF (5 mL). After 1 h stirring at 0° C. R-(+)-3,3,3-trifluoro-1,2-epoxypropane (500 mg, 4.46 mmol) was added to a 20 mL microwave vial via syringe. The closed vial was heated at 100° C. for 18 h. The reaction mixture was diluted with water and extracted twice with Et2O. The organic phase was washed with brine, dried over MgSO4, filtered and evaporated. Chromatography over silica (cyclohexane-EtOAc 95:5 to cyclohexane-EtOAc 75:25) afforded the title compound: ESIMS [M+NH4]+=268; 1H NMR (360 MHz, CDCl3): δ 7.29 (d, 2H), 6.94 (d, 2H), 4.56 (s, 2H), 4.15 (m, 1H), 3.87 (s, 3H), 3.74 (dd, 1H), 3.66 (dd, 1H), 2.88 (d, 1H).

Aufarbeitung

  1. temperatureThe closed vial was heated at 100° C. for 18 h
  2. extractionextracted twice with Et2O
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9839d77ad6414c189dca7fe7b151aff4
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093406B2

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