反应 #48632

反应方程式

isobutylmagnesium bromide

(2S)-(+)-glycidyl tosylate

→

desired compound

收率 75.5%

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

收率 75.5%

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   其他cannulate into the stirring Grignard reaction flask
2. 2
   其他Quench with saturated aqueous ammonium chloride (25 mL)
3. 3
   workup.ADDITIONpour supernate into saturated aqueous ammonium chloride (25 mL) and water
4. 4
   洗涤Wash with saturated aqueous sodium chloride
5. 5
   干燥dry (magnesium sulfate)
6. 6
   过滤filter
7. 7
   浓缩concentrate
8. 8
   其他purify
9. 9
   洗涤(silica gel chromatography, eluting with 10:90 to 25:75 ethyl acetate:hexanes)

实验过程

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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