반응 #43769

반응 방정식

DMAP

triethylamine

MsCl

nonanol

→

nonyl methanesulfonate

용매

DCM

반응 조건

후처리

1. 1
   기타at 0° C
2. 2
   기타After 15 minutes the cooling bath was removed
3. 3
   추출Extraction with water and DCM
4. 4
   기타afforded crude product that
5. 5
   기타was obtained
6. 6
   기타evaporation of the solvent under reduced pressure

실험 절차

500 mg (1.08 mmol) of (R)-9-(6-tert-butyl-dimethyl-silanyloxy)-2,5,7,8-tetramethylchroman-2-yl)nonanol was dissolved in dry DCM (10 ml) under argon atmosphere, followed by the addition of triethylamine (224 ul), MsCl (mesylchloride) (125 ul) and a catalytic amount of DMAP (dimethyl amino pyridine) at 0° C. After 15 minutes the cooling bath was removed and the reaction stirred at room temperature for 1.5 hours. TLC monitoring showed complete conversion in 100% DCM as mobile phase. Extraction with water and DCM afforded crude product that was obtained following evaporation of the solvent under reduced pressure. Column chromatography on silica (100% DCM) gave pure (R)-9-(6-tert-butyl-dimethyl-silanyloxy)-2,5,7,8-tetramethylchroman-2-yl)nonyl methanesulfonate in high yields (following high vacuum). (90%, 526 mg, 0.97 mmol)

출처