Diethyl Ether → HCID 20300759, 화합물

HRID 2193829

반응식

HRID 2193829 반응식
[CH2:1]([CH:3]([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:4][Mg]Br)[CH3:2].[CH2:11]([C:19]#N)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]CC.C([O:23][CH2:24][CH3:25])C>>[CH2:1]([CH:3]([CH2:4][C:24](=[O:23])[CH2:25][CH2:19][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:7][CH2:8][CH2:9][CH3:10])[CH3:2]

참가 물질

4

반응물 3

HCID 3283Diethyl Ether2회HCID 16715NonanenitrileHCID 178443576HCID 178443576, 화합물

생성물 1

HCID 20300759HCID 20300759, 화합물수율 32%

실험 절차

A Grignard solution of 2-ethylhexylmagnesiumbromide in diethylether (1.0 M, 110 mL, 0.11 mol) was slowly added via syringe to a stirred mixture of n-octylcyanide (4.66 g, 55 mmol) in diethyl ether (100 mL) at 0° C. under N2 atmosphere. After stirring for 12 h at reflux temperature, the reaction was quenched with an aqueous HCl-solution (2.0 M, 50 mL) at 0° C. and subsequently vigorously stirred for an additional 3 h at room temperature. The organic phase was separated and the aqueous phase was extracted with diethylether. The combined organic phases were washed with a saturated bicarbonate solution and brine, dried over MgSO4 and evaporated under reduced pressure to give a yellow solid. The resulting solid was purified by recrystallization from acetone to afford white crystals (IX) (4.51 g, 32%). 1H-NMR (CDCl3): δ=2.99-2.79 (m, 4H), 2.64-2.50 (m, 1H), 1.82-1.55 (m, 4H), 1.57-1.03 (m, 18H), 0.89-0.71 (m, 9H). 13C-NMR (CDCl3): δ=164.35, 34.89, 32.44, 30.31, 30.09, 29.90, 29.79, 28.48, 28.31, 25.71, 23.26, 14.71.

후처리

  1. temperatureat reflux temperature
  2. customthe reaction was quenched with an aqueous HCl-solution (2.0 M, 50 mL) at 0° C.
  3. stirringsubsequently vigorously stirred for an additional 3 h at room temperature
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted with diethylether
  6. washThe combined organic phases were washed with a saturated bicarbonate solution and brine
  7. dry with materialdried over MgSO4
  8. customevaporated under reduced pressure
  9. customto give a yellow solid
  10. customThe resulting solid was purified by recrystallization from acetone

출처 및 근거

ORD 기록
ord-3fd232368e534cef8c30e39de39357a3
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329923B2

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