反応 #1772019

反応方程式

(S)-benzyl 2-hydroxy-2-phenylacetate

triethylamine

p-toluenesulfonyl chloride

→

benzyl 2-phenyl-2-(tosyloxy)acetate

溶媒

CH2Cl2

CH2Cl2

反応条件

後処理

1. 1
   温度while maintaining the temperature between −5° C. and 0° C
2. 2
   workup.WAITstored in a freezer (−25° C.) for 14 hours
3. 3
   その他thaw to ambient temperature
4. 4
   洗浄washed with water (200 mL), 1N HCl (100 mL) and brine (100 mL)
5. 5
   乾燥dried (MgSO4)
6. 6
   ろ過filtered
7. 7
   濃縮concentrated in vacuo

実験手順

A CH2Cl2 (200 mL) solution of p-toluenesulfonyl chloride (8.65 g, 45.4 mmol) was added dropwise to a cooled (−5° C.) CH2Cl2 (200 mL) solution of (S)-benzyl 2-hydroxy-2-phenylacetate (10.0 g, 41.3 mmol), triethylamine (5.75 mL, 41.3 mmol) and 4-dimethylaminopyridine (0.504 g, 4.13 mmol), while maintaining the temperature between −5° C. and 0° C. The reaction was stirred at 0° C. for 9 hours, and then stored in a freezer (−25° C.) for 14 hours. It was allowed to thaw to ambient temperature and washed with water (200 mL), 1N HCl (100 mL) and brine (100 mL), dried (MgSO4), filtered, and concentrated in vacuo to provide benzyl 2-phenyl-2-(tosyloxy)acetate as a viscous oil which solidified upon standing (16.5 g). The chiral integrity of the product was not checked and that product was used for the next step without further purification. 1H NMR (DMSO-d6, δ=2.5, 500 MHz) δ 7.78 (d, J=8.6, 2H), 7.43-7.29 (m, 10H), 7.20 (m, 2H), 6.12 (s, 1H), 5.16 (d, J=12.5, 1H), 5.10 (d, J=12.5, 1H), 2.39 (s, 3H). RT=3.00 (Cond. III); >90% homogeneity index; LC/MS: Anal. Calcd. for [M+H]+ C22H20NaO5S: 419.09. found 419.04.

出典