Reacción #7772

Ecuación de reacción

(±)3,4-epoxytetrahydropyran

1-Methanesulfonyl-4-methylsulfanyl-benzene

nBuLi

NH4Cl

BF3 Et2O

→

(±)(3S*,4R*)-4-(4-methylsulfanyl-benzenesulfonylmethyl)-tetrahydro-pyran-3-ol

Rendimiento 35.9%

Disolventes

EtOAc

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter an addition 1 h at −78° C.
2. 2
   Temperaturathe solution was warmed to 0° C
3. 3
   workup.WAITAfter 2 h
4. 4
   Temperaturathe solution was cooled to −78° C.
5. 5
   TemperaturaThe solution was warmed to rt
6. 6
   LavadoThe organic layer was washed with brine
7. 7
   Otrodried
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated

Procedimiento

1-Methanesulfonyl-4-methylsulfanyl-benzene (4.33 g) was dissolved in THF (50 mL) and cooled to −78° C. prior to the addition of 1.6 M nBuLi (13.4 mL). After 0.5 h, BF3-Et2O (2.7 mL) was added followed (±)3,4-epoxytetrahydropyran (1.2 g) (Tetrahedron 1974, 4013). After an addition 1 h at −78° C., the solution was warmed to 0° C. After 2 h, the solution was cooled to −78° C. and saturated NH4Cl solution (aq) was added. The solution was warmed to rt and EtOAc was added. The organic layer was washed with brine, dried, filtered, and concentrated. Flash chromatography of the resulting residue gave (±)(3S*,4R*)-4-(4-methylsulfanyl-benzenesulfonylmethyl)-tetrahydro-pyran-3-ol (1.3 g) as the major product. MS found: (M+H)+=303.0.

Fuente