反応 #48632

反応方程式

isobutylmagnesium bromide

(2S)-(+)-glycidyl tosylate

→

desired compound

収率 75.5%

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

収率 75.5%

溶媒

tetrahydrofuran

反応条件

後処理

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

実験手順

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%).

出典