반응 #7732

반응 방정식

lithium diisopropylamide

methyl 4-fluorophenyl-acetate

2-methylsulfanyl-pyrimidine-4-carbaldehyde

→

desired product

수율 76.0%

2-(4-fluorophenyl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-3-hydroxypropionic acid methyl ester

수율 76.0%

용매

THF

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITIONis added dropwise to the reaction mixture
2. 2
   기타the reaction is quenched
3. 3
   workup.ADDITIONby pouring the reaction solution into aqueous saturated NH4Cl
4. 4
   추출The aqueous phase is extracted with ethyl acetate
5. 5
   건조dried (MgSO4)
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo
8. 8
   기타The crude residue is purified over silica (33% EtOAc/hexanes)

실험 절차

To a cold (−78° C.) solution of lithium diisopropylamide (21.4 mL of 2M solution in THF, 42.8 mmol) in THF (70 mL) is added dropwise a solution of methyl 4-fluorophenyl-acetate (6.0 g, 35.7 mmol) in THF (30 mL). The solution is stirred for 1 hour at −78° C. after which a solution of 2-methylsulfanyl-pyrimidine-4-carbaldehyde, 1, (6.0 g, 39.3 mmol) in THF (30 mL) is added dropwise to the reaction mixture. Stirring is continued for 45 minutes at −78° C. then the reaction is quenched by pouring the reaction solution into aqueous saturated NH4Cl. The aqueous phase is extracted with ethyl acetate. The organic phases combined, dried (MgSO4), filtered, and concentrated in vacuo. The crude residue is purified over silica (33% EtOAc/hexanes) to afford 8.7 g (76%) of the desired product as a mixture (1:1) of diastereomers.

출처