반응 #65938

반응 방정식

Tetramethyltin

3 -(N-Allyl-N-n-propylamino)-5 -trifluoromethane sulfonyloxychroman

LiCl

2.6-di- t-butyl- 4-methylphenol

→

5-acetyl-3-(N-allyl-N-n-propylamino)chroman

수율 39.0%

용매

DMF

THF n-hexane

반응 조건

후처리

1. 1
   기타The flask was evacuated
2. 2
   기타followed by inlet of CO (three times)
3. 3
   기타The solvent was evaporated
4. 4
   기타the residue was partitioned between aqueous NH3 (2M) and CH2Cl2 (3×15 mL)
5. 5
   건조the organic phases were dried (Na2SO4)
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo

실험 절차

3 -(N-Allyl-N-n-propylamino)-5 -trifluoromethane sulfonyloxychroman (0.28 g, 0.74 mmol), LiCl (0.097 g, 2.3 mmol), PdCl2 (dppf) (0.031 g, 0.04 retool) and 2.6-di- t-butyl- 4-methylphenol (0,005 g) were dissolved in DMF (5.0 mL) in a three-necked round-bottom flask (50 mL) with a magnetic stirrer. The flask was evacuated, followed by inlet of CO (three times). Tetramethyltin (0.12 mL, 0.89 mmol) was added and then the mixture was stirred under an atmosphere of CO (1 arm) at 120° C. (oilbath temp) for 4 hours. The solvent was evaporated, the residue was partitioned between aqueous NH3 (2M) and CH2Cl2 (3×15 mL) and the organic phases were dried (Na2SO4), filtered and concentrated in vacuo. Column chromatography on silica with THF-n-hexane (1:9) as eluent afforded 5-acetyl-3-(N-allyl-N-n-propylamino)chroman (0.078 g, 39% yield) as an oil. The base was precipitated from an ether solution by adding a slight excess of HCl (approx. 3M in ether). The crude salt was collected and dried in vacuo at 40° C. to give a white amorphous powder. Mp 125°-127° C. PdCl 2 (dppf)=dichloro[1,1'-bis(diphenylphosphino)-ferrocene] palladium (II).

출처