Reacción #48632

Ecuación de reacción

isobutylmagnesium bromide

(2S)-(+)-glycidyl tosylate

→

desired compound

Rendimiento 75.5%

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

Rendimiento 75.5%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrocannulate into the stirring Grignard reaction flask
2. 2
   OtroQuench with saturated aqueous ammonium chloride (25 mL)
3. 3
   workup.ADDITIONpour supernate into saturated aqueous ammonium chloride (25 mL) and water
4. 4
   LavadoWash with saturated aqueous sodium chloride
5. 5
   Secadodry (magnesium sulfate)
6. 6
   Filtraciónfilter
7. 7
   Concentraciónconcentrate
8. 8
   Otropurify
9. 9
   Lavado(silica gel chromatography, eluting with 10:90 to 25:75 ethyl acetate:hexanes)

Procedimiento

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%).

Fuente