Water → 2-(1-Methylethyl)-5,9-dimethyl-2,4,8-decatrienenitrile

HRID 5663

반응식

HRID 5663 반응식
C(OP([CH:9]([CH:12]([CH3:14])[CH3:13])[C:10]#[N:11])(OCC)=O)C.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:25][C:26](=[CH:28][CH2:29][CH2:30]/[C:31](=[CH:33]/[CH:34]=O)/[CH3:32])[CH3:27].O>C1(C)C=CC=CC=1.CCCCCC.C(OCC)(=O)C>[CH3:14][CH:12]([C:9](=[CH:34][CH:33]=[C:31]([CH3:32])[CH2:30][CH2:29][CH:28]=[C:26]([CH3:27])[CH3:25])[C:10]#[N:11])[CH3:13]

참가 물질

7

반응물 4

HCID 962WaterHCID 638011CitralHCID 3251421Potassium bis(trimethylsilyl)amideHCID 11031342Phosphonic acid, (1-cyano-2-methylpropyl)-, diethyl ester

생성물 1

HCID 540705132-(1-Methylethyl)-5,9-dimethyl-2,4,8-decatrienenitrile수율 90%

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 21226206Ethyl acetate hexane용매

반응 조건

온도
-70 °C

실험 절차

To a solution of 2-(diethylphosphono)isovaleronitrile (6.54 g, 30 mmol) in toluene (55 ml) was added a 0.5 M solution of potassium bis(trimethylsilyl)amide in toluene (56 ml) with stirring on a cooling bath at -70° C. After 30 minutes, geranial (3.80 g, 25 mmol) was added thereto with continuous stirring at the same temperature, and then the reaction mixture was warmed up to room temperature. After addition of water to the mixture, the organic layer was extracted. The organic extract was washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over MgSO4, and filtered. The filtrate was concentrated to give a residue, which was then subjected to silica gel column chromatography (solvent: n-hexane/ethyl acetate=100:1) to give 2-(1-methylethyl)-5,9-dimethyl-2,4,8-decatrienenitrile (4.87 g, 90%, 2Z:2E=22.4:1).

후처리

  1. stirringwith continuous stirring at the same temperature
  2. temperaturethe reaction mixture was warmed up to room temperature
  3. extractionthe organic layer was extracted
  4. extractionThe organic extract
  5. washwas washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customto give a residue, which

출처 및 근거

ORD 기록
ord-d8573869d08e470baf695611eb541645
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05245085

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