반응 #48642

반응 방정식

phenyl methyl magnesium bromide

(2S)-(+)-glycidyl tosylate

acetonitrile dry ice

→

desired compound

수율 50.0%

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

수율 50.0%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   기타quench with a saturated aqueous ammonium chloride solution
2. 2
   workup.ADDITIONdilute with diethyl ether
3. 3
   세척Wash the organic layer with saturated aqueous sodium chloride
4. 4
   건조dry (sodium sulfate)
5. 5
   농축concentrate
6. 6
   기타purify
7. 7
   세척(silica gel chromatography, eluting with 35:65 ethyl acetate:hexanes)

실험 절차

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%)

출처