Sodium borohydride → 1,1,1,5,5,5-Hexafluoro-3-pentanol

HRID 1421119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1421119
[BH4-].[Na+].[C:3]([CH2:7][C:8]([CH2:10][C:11]([F:14])([F:13])[F:12])=[O:9])([F:6])([F:5])[F:4]>O>[C:11]([CH2:10][CH:8]([CH2:7][C:3]([F:4])([F:5])[F:6])[OH:9])([F:14])([F:13])[F:12]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydride2×HCID 106316431,1,1,5,5,5-Hexafluoropentan-3-one

Produkt 1

HCID 108217011,1,1,5,5,5-Hexafluoro-3-pentanolAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium borohydride (0.8 g) was added to 15 ml water at 0 C. (ice bath). After the NaBH4 had dissolved, 9.7 g of CF3CH2C(O)CH2CF3 were added. The ketone froze. The ice bath was removed until the mixture was warm enough to melt the ketone, and the ice bath cooling was resumed. The reaction was quenched after 1 h with the addition of 5 ml 2N HCl and 10 ml brine. The lower layer (8.9 g) consisted of 95% pure CF3CH2CH(OH)CH2CF3 (91% yield). Distillation increased the purity to 97%; boiling point 65 C. at 95 mm Hg. 1H NMR: 4.4 (pentet, 1H), 2.9 (s, 1H), 2.4 (m, 4H) ppm. 19F NMR: -64.2 (t, J=10 Hz) ppm. FT-IR: 3415 (OH), 1264, 1154 cm-1. MS: 113 (64.8), 111 (18.6), 109 (10.8), 93 (91.4), 91 (14.2), 69(16.5), 65 (100), 64 (33.8), 49 (28.1), 29 (25.8). Anal. Calcd for C5H6F6O: C, 30.63; H, 3.08. Found: C, 30,61; H, 3.11.

Aufarbeitung

  1. customThe ice bath was removed until the mixture
  2. temperaturewas warm enough
  3. temperaturethe ice bath cooling
  4. customThe reaction was quenched after 1 h with the addition of 5 ml 2N HCl and 10 ml brine

Quellen und Nachweise

ORD-Eintrag
ord-480821798c4e40cc947c7a5c5d0d6dac
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06072088

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