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

HRID 5663

反応式

HRID 5663 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒2 回HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
-70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d8573869d08e470baf695611eb541645
出典データセット
uspto-grants-1993_09
特許番号
US05245085

関連ノート

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