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

HRID 1421119ノート

反応式

HRID 1421119 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 108217011,1,1,5,5,5-Hexafluoro-3-pentanol収率 91%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-480821798c4e40cc947c7a5c5d0d6dac
出典データセット
uspto-grants-2000_06
特許番号
US06072088

反応ノート

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