반응 #7771

반응 방정식

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

수율 80.3%

용매

THF

EtOAc

THF

반응 조건

후처리

1. 1
   workup.ADDITIONAfter an addition 1 h at −78° C.
2. 2
   온도the solution was warmed to 0° C
3. 3
   workup.WAITAfter 2 h
4. 4
   온도the solution was cooled to −78° C.
5. 5
   온도The solution was warmed to rt
6. 6
   세척The organic layer was washed with brine
7. 7
   기타dried
8. 8
   여과filtered
9. 9
   농축concentrated

실험 절차

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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