반응 #172360

반응 방정식

HCl

NaOH

2-(3-bromophenyl)-1,3-dioxane

2,6-dimethylmorpholine

NaOt-Bu

→

3-(2,6-dimethylmorpholino)benzaldehyde

수율 75.4%

용매

toluene

반응 조건

후처리

1. 1
   온도at reflux for 5 h
2. 2
   기타The resulting reaction mixture
3. 3
   workup.STIRRINGwas stirred at room temperature for 1 h
4. 4
   추출The aqueous mixture was extracted with CH2Cl2 (3×50 mL)
5. 5
   건조The combined organic layers were dried (MgSO4)
6. 6
   농축concentrated under reduced pressure
7. 7
   기타Purification by chromatography (petroleum ether:EtOAc=10:1)

실험 절차

A mixture containing 2-(3-bromophenyl)-1,3-dioxane (136; 2.0 g, 8.23 mmol), 2,6-dimethylmorpholine (122; 1.14 g, 9.88 mmol), Pd2(dba)3 (50 mg), NaOt-Bu (1.39 g, 14.0 mmol) and BINAP (100 mg) in 20 mL of toluene was stirred at reflux for 5 h. Upon cooling to room temperature, enough cold 1N HCl (50 mL) was added to adjust the pH The resulting reaction mixture was stirred at room temperature for 1 h. NaOH(aq) was added to adjust the pH=11. The aqueous mixture was extracted with CH2Cl2 (3×50 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. Purification by chromatography (petroleum ether:EtOAc=10:1) afforded 3-(2,6-dimethylmorpholino)benzaldehyde 137 as a yellow oil (1.36 g, yield: 72%).

출처