Reacción #91171

Ecuación de reacción

water

LiHMDS

methoxymethyl triphenyl phosphonium chloride

4-Benzyloxy-3,5-difluoro-benzaldehyde

→

title compound

Rendimiento 20.3%

(4-benzyloxy-3,5-difluoro-phenyl)-acetaldehyde

Rendimiento 20.3%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONthe solution was added
2. 2
   workup.STIRRINGThe mixture was stirred at room temperature for 3 hours
3. 3
   OtroAfter the termination of the reaction
4. 4
   Extracciónextracted with EtOAc
5. 5
   OtroThe organic layer was separated
6. 6
   Secadodried with MgSO4
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   Otropurified by column chromatography (eluent, EtOAc/Hex=1/5)
9. 9
   workup.DISSOLUTIONAfter the obtained product was dissolved in THF (7.68 mL)
10. 10
    workup.ADDITION2N HCl (3.84 mL) was added
11. 11
    workup.STIRRINGthe mixture was stirred at 70° C. for 5 hours
12. 12
    OtroAfter the termination of the reaction
13. 13
    Concentraciónthe reactant was concentrated under reduced pressure
14. 14
    workup.ADDITIONadded with water
15. 15
    Extracciónextracted with EtOAc
16. 16
    OtroThe organic layer was separated
17. 17
    Secadodried with MgSO4
18. 18
    Concentraciónconcentrated under reduced pressure
19. 19
    Otrothe purified by column chromatography (eluent, EtOAc/Hex=1/5)

Procedimiento

After methoxymethyl triphenyl phosphonium chloride (1.04 g, 3.02 mmol) was dissolved in anhydrous THF (9 mL), LiHMDS 1.0M THF solution (3 mL, 3.02 mmol) was added thereto at 0° C., and the mixture was stirred for 15 minutes. 4-Benzyloxy-3,5-difluoro-benzaldehyde (0.50 g, 2.01 mmol) obtained in Step B of Preparation Example 2 was dissolved in anhydrous THF (6 mL), and the solution was added thereto. The mixture was stirred at room temperature for 3 hours. After the termination of the reaction, the reactant was added with water, and then extracted with EtOAc. The organic layer was separated, dried with MgSO4, concentrated under reduced pressure, and then purified by column chromatography (eluent, EtOAc/Hex=1/5). After the obtained product was dissolved in THF (7.68 mL), 2N HCl (3.84 mL) was added thereto, and the mixture was stirred at 70° C. for 5 hours. After the termination of the reaction, the reactant was concentrated under reduced pressure, added with water, and then extracted with EtOAc. The organic layer was separated, dried with MgSO4, concentrated under reduced pressure, and the purified by column chromatography (eluent, EtOAc/Hex=1/5) to obtain the title compound (0.107 g, 20%).

Fuente