反应 #217554

反应方程式

Water

[(1,1-dimethyl-2-oxobutyl)thio]acetic acid

phenyltrimethylammonium tribromide

→

[(3-bromo-1,1-dimethyl-2-oxobutyl)thio]acetic acid

溶剂

CH2Cl2

反应条件

后处理

1. 1
   其他to come to room temperature
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITwas continued for 1 h
4. 4
   萃取the aqueous layer was extracted with diethyl ether (15 ml)
5. 5
   洗涤The combined organic layers were washed with brine (25 ml)
6. 6
   干燥dried over Na2SO4
7. 7
   过滤filtered
8. 8
   浓缩concentrated in vacuo
9. 9
   其他The remaining oil was purified by flash chromatography (ethyl acetate-petroleum ether 1:1 containing 0.1% glacial acetic acid)

实验过程

To a solution of [(1,1-dimethyl-2-oxobutyl)thio]acetic acid (0.3 g, 1.58 mmol) in CH2Cl2 (10 ml) was added phenyltrimethylammonium tribromide (0.62 g, 1.65 mmol) at 0° C. After stirring for 15 min, the solution was allowed to come to room temperature and stirring was continued for 1 h. Water (30 ml) was added and the aqueous layer was extracted with diethyl ether (15 ml). The combined organic layers were washed with brine (25 ml), dried over Na2SO4, filtered and concentrated in vacuo. The remaining oil was purified by flash chromatography (ethyl acetate-petroleum ether 1:1 containing 0.1% glacial acetic acid). Yield: 0.39 mg (91%). 1H-NMR (400 MHz, CDCl3): δ=1.15, 1.64 (2×s, 6H, C(CH3)2), 1.81 (d, 3H, J=7.0 Hz), 3.14, 3.21 (2×d, 2H, J=6.8 Hz), 5.07 (q, 1H, J=7.0 Hz) ppm. C8H13BrO3S (269.16, 267.98), HRMS: calcd (M+Na)+ 290.9661, found 290.9669.

来源