反应 #2307986

反应方程式

HOBt

2-methyl-2-[2-(2,6,6-trimethyl-cyclohex-1-enyl)-ethyl]-[1,3]oxazinane

2-Methyl-2-[2-(2,6,6-trimethyl-cyclohex-1-enyl)-ethyl]-[1,3]oxazinane

3-(2,4-dihydroxy-phenyl)-3-methyl-acrylic acid

DCC

→

3-(2,4-Dihydroxy-phenyl)-1-{2-methyl-2-[2-(2,6,6-trimethyl-cyclohex-1-enyl)-ethyl]-[1,3]oxazinan-3-yl}-but-2-en-1-one

溶剂

THF

反应条件

后处理

1. 1
   workup.STIRRINGstirred at 0° C. for 1 h
2. 2
   workup.STIRRINGstirred for an additional 24 h
3. 3
   温度The mixture is cooled to 0° C.
4. 4
   过滤filtered
5. 5
   其他the solvent is removed in vacuo
6. 6
   workup.ADDITIONThe residue is diluted with ethyl acetate
7. 7
   洗涤washed three times with saturated sodium bicarbonate
8. 8
   干燥The organic layer is dried over anhydrous magnesium sulfate
9. 9
   过滤filtered
10. 10
    浓缩concentrated in vacuo
11. 11
    其他The product 9 is further purified by flash chromatography on basic alumina with 20:1 chloroform/methanol

实验过程

To a 0° C. solution of 11.1 g (0.050 mol) of 3-(2,4-dihydroxy-phenyl)-3-methyl-acrylic acid in 500 mL of anhydrous THF is added 10.3 g (0.050 mol) of DCC. After stirring for 10 min, 6.8 g (0.050 mol) of HOBt, 11.3 g (0.045 mol) of 2-methyl-2-[2-(2,6,6-trimethyl-cyclohex-1-enyl)-ethyl]-[1,3]oxazinane (8) and 1.1 g (0.009 mol) of DMAP are added and stirred at 0° C. for 1 h, warmed to room temperature and stirred for an additional 24 h. The mixture is cooled to 0° C., filtered and the solvent is removed in vacuo. The residue is diluted with ethyl acetate and washed three times with saturated sodium bicarbonate, followed by 10% citric acid and brine. The organic layer is dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The product 9 is further purified by flash chromatography on basic alumina with 20:1 chloroform/methanol.

来源