Reacción #50794

Ecuación de reacción

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

lithium hexamethyldisilazane

lithium hexamethyldisilazane

1-bromo-2-chloroethane

1-(carboethoxy)-1-(4-methoxybenzylthio)methane

→

1-(carboethoxy)-1-(4-methoxybenzylthio)cyclopropane

Rendimiento 21.0%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAdd, by cannula transfer
2. 2
   workup.STIRRINGstir to room temperature overnight
3. 3
   workup.STIRRINGstir at room temperature for 24 hours
4. 4
   OtroQuench with saturated ammonium chloride (5 mL)
5. 5
   Otropartition between ethyl acetate (30 mL) and water (30 mL)
6. 6
   OtroSeparate the organic phase
7. 7
   Secadodry (Na2SO4)
8. 8
   Otroevaporate the solvent in vacuo
9. 9
   OtroPurify by chromatography (5:1 hexane/ethyl acetate to 2.5:1 hexane/ethyl acetate)

Procedimiento

Cool lithium hexamethyldisilazane (6 mL of a 1.0M solution in tetrahydrofuran, 6.0 mmol) to -78° C. Add, by cannula transfer, a solution of 1-(carboethoxy)-1-(4-methoxybenzylthio)methane (1.36 g, 5.66 mmol) in tetrahydrofuran (10 mL). Stir for 45 minutes, add 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) (0.73 mL, 6.0 mmol) followed by 1-bromo-2-chloroethane (050 mL, 6.0 mmol) and stir to room temperature overnight. Cool to -78° C., add lithium hexamethyldisilazane (6.0 mL, 6.0 mmol) and stir at room temperature for 24 hours. Quench with saturated ammonium chloride (5 mL) and partition between ethyl acetate (30 mL) and water (30 mL). Separate the organic phase, dry (Na2SO4) and evaporate the solvent in vacuo. Purify by chromatography (5:1 hexane/ethyl acetate to 2.5:1 hexane/ethyl acetate) to give 1-(carboethoxy)-1-(4-methoxybenzylthio)cyclopropane (317 mg, 21%).

Fuente