반응 #48632

반응 방정식

isobutylmagnesium bromide

(2S)-(+)-glycidyl tosylate

→

desired compound

수율 75.5%

Toluene-4-sulfonic acid 2-(S)-hydroxy-5-methylhexyl ester

수율 75.5%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   기타cannulate into the stirring Grignard reaction flask
2. 2
   기타Quench with saturated aqueous ammonium chloride (25 mL)
3. 3
   workup.ADDITIONpour supernate into saturated aqueous ammonium chloride (25 mL) and water
4. 4
   세척Wash with saturated aqueous sodium chloride
5. 5
   건조dry (magnesium sulfate)
6. 6
   여과filter
7. 7
   농축concentrate
8. 8
   기타purify
9. 9
   세척(silica gel chromatography, eluting with 10:90 to 25:75 ethyl acetate:hexanes)

실험 절차

Add dropwise over 5 minutes isobutylmagnesium bromide (4.4 mL, 8.8 mmol, 2 M in diethyl ether) to a solution of lithium tetrachlorocuprate (4.4 mL, 0.44 mmol, 0.1 M in tetrahydrofuran) cooled to −35-40° C. Dissolve (2S)-(+)-glycidyl tosylate (1.674 g, 7.73 mmol) in tetrahydrofuran (8 mL), cool to −40° C. and cannulate into the stirring Grignard reaction flask. Quench with saturated aqueous ammonium chloride (25 mL), pour supernate into saturated aqueous ammonium chloride (25 mL) and water and shake well. Wash with saturated aqueous sodium chloride, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 10:90 to 25:75 ethyl acetate:hexanes) to give the desired compound (1.6711 g, 75%).

출처