Réaction #52038

Équation de réaction

THF

3-[2,2-Difluoro-2-(4′-methoxy-biphenyl-4-yl)-ethyl]-5-phenylsulfanylmethyl-dihydro-furan-2-one

phenylthiol

BuLi

THF

→

desired compound

2-[2,2-Difluoro-2-(4′-methoxy-biphenyl-4-yl)-ethyl]-4-hydroxy-5-phenylsulfanyl-pentanoic acid

Conditions de réaction

Traitement

1. 1
   Températureto warm to 0° C.
2. 2
   workup.WAITkept at that temperature for 2 hours
3. 3
   Températureis warmed up to room temperature
4. 4
   workup.STIRRINGstirred for 3 hours
5. 5
   AutreThe reaction is quenched with saturated NH4Cl
6. 6
   Extractionextracted with ethyl acetate
7. 7
   LavageThe combined organic layers are washed with brine
8. 8
   Séchagedried over MgSO4
9. 9
   AutreThe crude material obtained
10. 10
    Autreafter evaporation of solvents
11. 11
    Autreis purified by flash chromatography (3/1 hexane/acetone)
12. 12
    Autrerecrystallized from hexane/acetone

Mode opératoire

3-[2,2-Difluoro-2-(4′-methoxy-biphenyl-4-yl)-ethyl]-5-phenylsulfanylmethyl-dihydro-furan-2-one. A solution of phenylthiol (0.65 mmol) in THF (5 mL) is treated with BuLi (0.65 mmol) at −20° C. After being stirred for 20 min at −20° C., Example 18d (0.5 mmol) in THF (5 mL) is added dropwise. The mixture is allowed to warm to 0° C. and kept at that temperature for 2 hours, then is warmed up to room temperature and stirred for 3 hours. The reaction is quenched with saturated NH4Cl, neutralized with 1N HCl and extracted with ethyl acetate. The combined organic layers are washed with brine and dried over MgSO4. The crude material obtained after evaporation of solvents is purified by flash chromatography (3/1 hexane/acetone) and recrystallized from hexane/acetone to give the desired compound as colorless needles: mp 117-118° C.

Source