Реакция #728769

Уравнение реакции

HCl

BF3.Et2O

3,4-epoxytetrahydropyran

n-BuLi

1-Methanesulfonyl-4-methylsulfanyl-benzene

→

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

Выход 20.2%

Растворители

THF

hexane

EtOAc

THF

Условия реакции

Обработка

1. 1
   workup.ADDITIONAfter an addition 1 h at −78° C.
2. 2
   Температураthe solution was warmed to 0° C
3. 3
   workup.WAITAfter 2 h
4. 4
   Температураthe solution was cooled to −78° C.
5. 5
   ТемператураThe solution was warmed to rt
6. 6
   ПромывкаThe organic layer was washed with brine
7. 7
   Другоеdried
8. 8
   Фильтрацияfiltered
9. 9
   Концентрированиеconcentrated

Методика

1-Methanesulfonyl-4-methylsulfanyl-benzene (4.3 g) was dissolved in THF (40 ml) and cooled to −78° C. prior to the slow addition of 1.6 M n-BuLi in hexane (13.4 ml). After 0.5 h, BF3.Et2O (2.7 ml) was added followed by 3,4-epoxytetrahydropyran (2.2 g) (Berti et al. Tetrahedron 1974, 30, 4013) (2.3 g) in THF (20 ml). 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 1N HCl 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.

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