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

HRID 1421119Notes

Reaction equation

HRID 1421119 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-480821798c4e40cc947c7a5c5d0d6dac
Source dataset
uspto-grants-2000_06
Patent number
US06072088

Reaction notes

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