تفاعل #462655

معادلة التفاعل

sodium hydroxide

(4RS,4aSR,7aRS)-4-hydroxy4-phenyl-6-benzylperhydrothiopyrano[2,3-c]pyrrole

→

(4aRS,7aRS)-6-benzyl-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole

المردود 85.8%

المذيبات

benzene

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture is refluxed for 1 hour
2. 2
   أخرىbrought to 20° C.
3. 3
   درجة الحرارةcooled solution
4. 4
   أخرىThe suspension obtained
5. 5
   ترشيحis filtered
6. 6
   أخرىthe filtrate is decanted
7. 7
   غسيلthe organic phase is washed with 200 cm3 of a saturated aqueous solution of sodium chloride
8. 8
   تجفيفdried over magnesium sulphate
9. 9
   تركيزconcentrated to dryness under reduced pressure (2.7 kPa)
10. 10
    أخرىThe oil obtained
11. 11
    أخرىis chromatographed on a silica gel column (0.04 mm-0.06 mm, diameter 5.2 cm, height 39 cm)
12. 12
    غسيلeluting under a nitrogen pressure of 0.6 bar
13. 13
    أخرىwith a cyclohexane and ethyl acetate mixture (90/10 by volume) and collecting fractions of 125 cm 3
14. 14
    تركيزconcentrated to dryness under reduced pressure (2.7 kPa)
15. 15
    أخرىThe oil obtained
16. 16
    أخرىis crystallized from 200 cm3 of diisopropyl oxide
17. 17
    أخرىdried

الإجراء التجريبي

43.7 g of zirconium tetrachloride are added to a solution of 12.2 g of (4RS,4aSR,7aRS)-4-hydroxy4-phenyl-6-benzylperhydrothiopyrano[2,3-c]pyrrole in 180 cm3 of benzene. The reaction mixture is refluxed for 1 hour and then brought to 20° C. and diluted with 200 cm3 of dichloromethane. 150 cm3 of a 4N aqueous solution of sodium hydroxide are added to the resulting cooled solution. The suspension obtained is filtered, the filtrate is decanted, the organic phase is washed with 200 cm3 of a saturated aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The oil obtained is chromatographed on a silica gel column (0.04 mm-0.06 mm, diameter 5.2 cm, height 39 cm), eluting under a nitrogen pressure of 0.6 bar, with a cyclohexane and ethyl acetate mixture (90/10 by volume) and collecting fractions of 125 cm 3. Fractions 19 to 32 are pooled and concentrated to dryness under reduced pressure (2.7 kPa). The oil obtained is crystallized from 200 cm3 of diisopropyl oxide, the crystals are drained and dried. 6.2 g of (4aRS,7aRS)-6-benzyl-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole are obtained in the form of orange-colored crystals; melting point 130° C.

المصدر