Sulfuric Acid → Ethyl 3-cyano-4,4,5,5,5-pentafluoro-3-hydroxypentanoate

HRID 2387243

反応式

HRID 2387243 の反応式
[C-:1]#[N:2].[K+].[F:4][C:5]([F:18])([C:14]([F:17])([F:16])[F:15])[C:6](=[O:13])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].S(=O)(=O)(O)O>O.CCO>[C:1]([C:6]([OH:13])([C:5]([F:18])([F:4])[C:14]([F:15])([F:16])[F:17])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])#[N:2]

参加物

6

反応物 3

HCID 1118Sulfuric AcidHCID 9032Potassium CyanideHCID 522203Ethyl 4,4,5,5,5-Pentafluoro-3-oxovalerate

生成物 1

HCID 86646544Ethyl 3-cyano-4,4,5,5,5-pentafluoro-3-hydroxypentanoate

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of KCN (1.4 eq.) in water (0.5 M) was added with stirring to an ice-cooled solution of ethyl 4,4,5,5,5-pentafluoro-3-oxopentanoate (1 eq.) in EtOH and water (40:60 vol). The mixture was stirred for 6 h at 0° C. and then acidified with 6N sulphuric acid and extracted with Et2O. The organic phase was dried (Na2SO4), and the solvents were removed under reduced pressure. The residue was vacuum distilled. The product fraction was collected at 74-76° C./0.5 mbar. (400 MHz, CDCl3) δ: 5.88 (1H, s), 4.40-4.23 (2H, m), 3.04 (1H, s), 1.33 (3H, t, J=7.1 Hz).

後処理

  1. extractionextracted with Et2O
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customthe solvents were removed under reduced pressure
  4. distillationdistilled
  5. customThe product fraction was collected at 74-76° C./0.5 mbar

出典と根拠

ORDレコード
ord-8896f9ccbbb048a8acabd0b92b467d4a
出典データセット
uspto-grants-2012_09
特許番号
US08268827B2

関連ノート

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