反応 #57514

反応方程式

Water

tert-butyldimethylchlorosilane

(2,4-Dihydroxy-phenyl)-oxo-acetic acid ethyl ester

triethylamine

→

mono-substituted product

収率 40.0%

[4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-phenyl]-oxo-acetic acid ethyl ester

収率 40.0%

溶媒

DCM

DCM

反応条件

後処理

1. 1
   その他to quench
2. 2
   その他the reaction
3. 3
   洗浄The organic layer was washed with water (2×30 mL)
4. 4
   乾燥dried over Na2SO4
5. 5
   ろ過filtrated
6. 6
   濃縮concentrated under reduced pressure

実験手順

To a solution of (2,4-Dihydroxy-phenyl)-oxo-acetic acid ethyl ester (from step 1, 2.71 g, 12.9 mmol, 1 eq) in anhydrous DCM (40 mL) solution was added triethylamine (1.97 mL, 14.2 mmol, 1.1 eq), followed by addition of tert-butyldimethylchlorosilane (1.89 g, 14.2 mmol, 1.1 eq)/DCM (10 mL) solution dropwise at 0° C. under argon. The reaction mixture was stirred at 0° C. for 5 min. Water (30 mL) was added to the reaction mixture to quench the reaction. The organic layer was washed with water (2×30 mL), dried over Na2SO4, filtrated, and concentrated under reduced pressure to afford a light yellow solid (4.1 g, contains 40% mono-substituted product) as crude product. This material was used in step 3 without further purification.

出典