반응 #5761

반응 방정식

farnesol

2-(diethylphosphono)isovaleronitrile

potassium bis(trimethylsilyl)amide

water

→

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

수율 96.0%

용매

toluene

toluene

반응 조건

후처리

1. 1
   기타The cooling bath was removed
2. 2
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 30 minutes
3. 3
   온도The reaction mixture was cooled to -70° C. again
4. 4
   workup.STIRRINGwith stirring
5. 5
   온도to warm to room temperature
6. 6
   기타the organic layer was separated
7. 7
   세척washed with saturated aqueous sodium bicarbonate
8. 8
   건조saturated aqueous sodium chloride, and dried over MgSO4
9. 9
   기타The organic layer was separated from MgSO4 by filtration
10. 10
    농축concentrated
11. 11
    기타to give a residue, which
12. 12
    기타was purified with silica gel column chromatography (solvent: n-hexane/ethyl acetate=100:1)

실험 절차

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).

출처