반응 #2710

반응 방정식

2,2-dimethyl-6-bromo-thiochroman-4-one

Compound M

2,2-dimethyl-6-bromo-thiochroman-4-one

pTSA

4-bromotoluene

t-BuLi

pentane

→

title compound

2,2-Dimethyl-4(tol-4-yl)-6-bromo-thiochrom-3-ene

용매

THF

ethylacetate

dichloromethane

THF

반응 조건

후처리

1. 1
   workup.ADDITIONThis mixture was added to a flask
2. 2
   workup.STIRRINGand stirred for 16 hours at ambient temperature
3. 3
   기타The reaction was quenched
4. 4
   workup.ADDITIONby adding aq. NH4Cl
5. 5
   추출the resulting mixture was extracted with ethylacetate
6. 6
   세척washed with brine
7. 7
   기타dried
8. 8
   기타the solvent was removed by evaporation
9. 9
   기타The product was isolated by chromatography on silica gel
10. 10
    온도heated to 50° C. for 3 hours
11. 11
    세척washed with 10% NaHCO3 (5 mL), brine (5 mL)
12. 12
    건조dried with MgSO4
13. 13
    기타the solvent was removed by evaporation

실험 절차

To a cold (-78° C.) solution of 4-bromotoluene (720 mg, 4.2 mmol) in THF (8 mL) was added t-BuLi in pentane (1.7M, 0.5 mL, 0.85 mmol). The mixture was warmed to ambient temperature over 30 minutes with stirring. This mixture was added to a flask containing 2,2-dimethyl-6-bromo-thiochroman-4-one (Compound M, 140 mg, 0.4 mmol) and THF (2 mL). and stirred for 16 hours at ambient temperature. The reaction was quenched by adding aq. NH4Cl, and the resulting mixture was extracted with ethylacetate, washed with brine, dried and the solvent was removed by evaporation. The product was isolated by chromatography on silica gel. The material was dissolved in dichloromethane (5 mL) and pTSA (5 mg) was added and heated to 50° C. for 3 hours. The misture was diluted with ethylacetate (20 mL), washed with 10% NaHCO3 (5 mL), brine (5 mL), dried with MgSO4 and the solvent was removed by evaporation to afford the title compound as an off.

출처