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

HRID 2387243

반응식

HRID 2387243 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매2회

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8896f9ccbbb048a8acabd0b92b467d4a
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268827B2

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