반응 #5353

반응 방정식

8-carbomethoxyoctanal

4-chlorobenzyltriphenylphosphonium chloride

water

potassium hexamethyldisilazide

→

10-(4-chlorophenyl)-dec-9-enoic acid methyl ester

수율 13.0%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONis added dropwise
2. 2
   온도to warm to room temperature
3. 3
   workup.STIRRINGstirred for 2 days
4. 4
   추출extracting three times with diethyl ether
5. 5
   세척washed with brine
6. 6
   건조dried over Na2SO4
7. 7
   여과filtered
8. 8
   농축concentrated in vacuo
9. 9
   기타to give a yellow solid
10. 10
    여과Pad filtration through flash silica gel eluting with 10% ethyl acetate/hexane
11. 11
    기타gives a yellow oil
12. 12
    농축after concentration in vacuo
13. 13
    세척Flash chromatography on a 60 mm×150 mm silica column eluting with 5% ethyl acetate/hexane

실험 절차

To a solution of 18.2 g (43 mmol) of 4-chlorobenzyltriphenylphosphonium chloride in 200 mL of dry tetrahydrofuran at -78° C. is added dropwise, 30.7 mL (43 mmol) of a 1.4M solution of potassium hexamethyldisilazide in tetrahydrofuran. This is allowed to stir for 1 hour when 8.0 g (43 mmol) of 8-carbomethoxyoctanal is added dropwise. The solution is stirred at -78° C. for 2 hours, allowed to warm to room temperature, and stirred for 2 days. The reaction is worked up by adding water and extracting three times with diethyl ether. The ether extracts are combined, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give a yellow solid. Pad filtration through flash silica gel eluting with 10% ethyl acetate/hexane, gives a yellow oil after concentration in vacuo. Flash chromatography on a 60 mm×150 mm silica column eluting with 5% ethyl acetate/hexane gives 1.62 g (13%) of 10-(4-chlorophenyl)-dec-9-enoic acid methyl ester as a mixture of E and Z isomers.

출처