تفاعل #5761

معادلة التفاعل

farnesol

2-(diethylphosphono)isovaleronitrile

potassium bis(trimethylsilyl)amide

water

→

2 -(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile

المردود 96.0%

المذيبات

toluene

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىThe cooling bath was removed
2. 2
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 30 minutes
3. 3
   درجة الحرارةThe reaction mixture was cooled to -70° C. again
4. 4
   workup.STIRRINGwith stirring
5. 5
   درجة الحرارةto warm to room temperature
6. 6
   أخرىthe organic layer was separated
7. 7
   غسيلwashed with saturated aqueous sodium bicarbonate
8. 8
   تجفيفsaturated aqueous sodium chloride, and dried over MgSO4
9. 9
   أخرىThe organic layer was separated from MgSO4 by filtration
10. 10
    تركيزconcentrated
11. 11
    أخرىto give a residue, which
12. 12
    أخرىwas purified with silica gel column chromatography (solvent: n-hexane/ethyl acetate=100:1)

الإجراء التجريبي

To a solution of 2-(diethylphosphono)isovaleronitrile (8.72 g, 40 mmol) in toluene (75 ml) was gradually added a 0.5 M 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).

المصدر