Water → 2-(1-Methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile

HRID 1464467

反応式

HRID 1464467 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+].O[CH2:26][CH:27]=[C:28]([CH2:30][CH2:31][CH:32]=[C:33]([CH2:35][CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39])[CH3:34])[CH3:29].O>C1(C)C=CC=CC=1>[CH3:14][CH:12]([C:9](=[CH:26][CH:27]=[C:28]([CH3:29])[CH2:30][CH2:31][CH:32]=[C:33]([CH3:34])[CH2:35][CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39])[C:10]#[N:11])[CH3:13]

参加物

6

反応物 4

HCID 962WaterHCID 3327a FarnesolHCID 3251421Potassium bis(trimethylsilyl)amideHCID 11031342Phosphonic acid, (1-cyano-2-methylpropyl)-, diethyl ester

生成物 1

HCID 536571452-(1-Methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile収率 96%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
-70 °C

実験手順

To a solution of 2-(diethylphosphono)isovaleronitrile (8.72 g, 40 mmol) in toluene (75 ml) was gradually added a 0.5M solution of potassium bis(trimethylsilyl)amide in toluene (75 ml) with stirring at -70° C. under argon atmosphere. The cooling bath was removed, and the reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was cooled to -70° C. again, and farnesol (5.88 g, 26.7 mmol) was added thereto with stirring, and the mixture was allowed to warm to room temperature. After addition of water, the organic layer was separated, washed with saturated aqueous sodium bicarbonate and then saturated aqueous sodium chloride, and dried over MgSO4. The organic layer was separated from MgSO4 by filtration and concentrated to give a residue, which was purified with silica gel column chromatography (solvent: n-hexane/ethyl acetate=100:1) to obtain the aimed 2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile (7.23 g, 96%; 2Z:2E=25.6:1).

後処理

  1. customThe cooling bath was removed
  2. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  3. temperatureThe reaction mixture was cooled to -70° C. again
  4. stirringwith stirring
  5. temperatureto warm to room temperature
  6. customthe organic layer was separated
  7. washwashed with saturated aqueous sodium bicarbonate
  8. dry with materialsaturated aqueous sodium chloride, and dried over MgSO4
  9. customThe organic layer was separated from MgSO4 by filtration
  10. concentrationconcentrated
  11. customto give a residue, which
  12. customwas purified with silica gel column chromatography (solvent: n-hexane/ethyl acetate=100:1)

出典と根拠

ORDレコード
ord-37dc4a52a34645e88271e6a6576e60d1
出典データセット
uspto-grants-1994_04
特許番号
US05304661

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