반응 #58849

반응 방정식

3-(3-bromophenyl)propionaldehyde

n-BuLi

→

1-bromo-3-but-3-enylbenzene

수율 50.0%

용매

THF

THF

반응 조건

후처리

1. 1
   온도cooled to −78° C.
2. 2
   workup.STIRRINGstirred at −78° C. for 1 h
3. 3
   온도to warm to room temperature
4. 4
   기타quenched with aqueous NH4Cl
5. 5
   농축concentrated under reduced pressure
6. 6
   세척washed sequentially with water and brine
7. 7
   건조dried over Na2SO4
8. 8
   농축concentrated under reduced pressure
9. 9
   농축Chromatography of this concentrate on silica gel with a gradient of 0.5% EtOAc-hexanes to 2.0% EtOAc-hexanes

실험 절차

A solution of 1.34 gm (3.77 mmol) of methyltriphenylphosphonium bromide in THF at 0° C. was treated dropwise with 2.3 mL of 1.6 M n-BuLi in hexanes (3.77 mmol), stirred at 0° C. for 0.25 h, cooled to −78° C., treated dropwise with a solution of 3-(3-bromophenyl)propionaldehyde (0.7 gm, 3.28 mmol) in THF, stirred at −78° C. for 1 h, allowed to warm to room temperature, quenched with aqueous NH4Cl and concentrated under reduced pressure. The resultant residue was taken up in EtOAc, washed sequentially with water and brine, dried over Na2SO4 and concentrated under reduced pressure. Chromatography of this concentrate on silica gel with a gradient of 0.5% EtOAc-hexanes to 2.0% EtOAc-hexanes gave 1-bromo-3-but-3-enylbenzene as an oil, 0.35 gm (50% yield); 1H NMR (400 MHz, CDCl3) δ: 2.33 (m, 2H), 2.66 (t, 2H, J=7.4 Hz), 4.98 (m, 2H), 5.79 (m, 1H), 7.12 (m, 2H), 7.30 (m, 2H).

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