反応 #48642

反応方程式

phenyl methyl magnesium bromide

(2S)-(+)-glycidyl tosylate

acetonitrile dry ice

→

desired compound

収率 50.0%

Toluene-4-sulfonic acid (S)-2-hydroxy-4-phenylbutyl ester

収率 50.0%

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   その他quench with a saturated aqueous ammonium chloride solution
2. 2
   workup.ADDITIONdilute with diethyl ether
3. 3
   洗浄Wash the organic layer with saturated aqueous sodium chloride
4. 4
   乾燥dry (sodium sulfate)
5. 5
   濃縮concentrate
6. 6
   その他purify
7. 7
   洗浄(silica gel chromatography, eluting with 35:65 ethyl acetate:hexanes)

実験手順

Add phenyl methyl magnesium bromide (14 mL, 14 mmol, 1 M in tetrahydrofuran) to a solution of lithium tetrachlorocuprate (5.5 mL, 0.55 mmol, 0.1 M in tetrahydrofuran) in dry tetrahydrofuran (10 mL) and stir at −35° C. (acetonitrile/dry ice bath) for 15 minutes (J. Med. Chem., 41, 2451-2460, (1998); JOC, 54, 1295-1304, (1989)). Cool to −35° C. a solution of (2S)-(+)-glycidyl tosylate (2.51 g, 11.0 mmol) in dry tetrahydrofuran (4 mL) and transfer rapidly via cannula to the Grignard solution. Stir for 1 hour at −35° C., quench with a saturated aqueous ammonium chloride solution and dilute with diethyl ether. Wash the organic layer with saturated aqueous sodium chloride, dry (sodium sulfate), concentrate and purify (silica gel chromatography, eluting with 35:65 ethyl acetate:hexanes) to give the desired compound as a colorless oil (1.77 g, 50%)

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