Реакция #48632

Уравнение реакции

isobutylmagnesium bromide

(2S)-(+)-glycidyl tosylate

→

desired compound

Выход 75.5%

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

Выход 75.5%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Другоеcannulate into the stirring Grignard reaction flask
2. 2
   ДругоеQuench with saturated aqueous ammonium chloride (25 mL)
3. 3
   workup.ADDITIONpour supernate into saturated aqueous ammonium chloride (25 mL) and water
4. 4
   ПромывкаWash with saturated aqueous sodium chloride
5. 5
   Сушкаdry (magnesium sulfate)
6. 6
   Фильтрацияfilter
7. 7
   Концентрированиеconcentrate
8. 8
   Другоеpurify
9. 9
   Промывка(silica gel chromatography, eluting with 10:90 to 25:75 ethyl acetate:hexanes)

Методика

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%).

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