Реакция #7771

Уравнение реакции

NH4Cl

BF3 Et2O

(±)(1S*,2R*,4S*)-4-(benzyloxy)-1,2-epoxycyclohexane

1-Methanesulfonyl-4-methylsulfanyl-benzene

nBuLi

→

(±)(1R*,2R*,5S*)-5-benzyloxy-2-(4-methylsulfanyl-benzenesulfonylmethyl)-cyclohexanol

Выход 80.3%

Растворители

THF

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 (3.25 g) was dissolved in THF (50 mL) and cooled to −78° C. prior to the addition of 1.6 M nBuLi (10 mL). After 0.5 h, BF3-Et2O (2.04 mL) was added followed by (±)(1S*,2R*,4S*)-4-(benzyloxy)-1,2-epoxycyclohexane (2.19 g) (Chini et al. J. Org. Chem. 1990, 55, 4265) 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 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 (±)(1R*,2R*,5S*)-5-benzyloxy-2-(4-methylsulfanyl-benzenesulfonylmethyl)-cyclohexanol (3.5 g) as the major product: 1H NMR (CDCl3, δ ppm, 300 mHz) 1.41 (m, 2H), 1.59 (m, 1H), 1.95 (m, 1H), 2.05-2.35 (m, 2H), 2.54 (s, 3H), 2.96 (dd, 1H), 3.64 (m, 2H), 3.81 (s, 1H), 4.48 (m, 2H), 7.3 (m, 7H), 7.82 (d, 2H)

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