反应 #1985938

反应方程式

2-tert-butyldimethylsilyloxymethyl-4-trimethylacetyloxybromobenzene

→

desired product

Methyl 2-Tert-butyldimethylsilyloxymethyl-4-trimethylacetyloxycinnamate

溶剂

dimethylformamide

反应条件

后处理

1. 1
   其他The resulting solution is degassed
2. 2
   workup.ADDITIONdry triethylamine (67 ml) added
3. 3
   温度cooled
4. 4
   workup.ADDITIONdiluted with ether
5. 5
   洗涤washed with water
6. 6
   干燥dried over magnesium sulfate
7. 7
   过滤filtered
8. 8
   浓缩concentrated under reduced pressure
9. 9
   其他The residue is purified by flash chromatography
10. 10
    洗涤eluting with 10% ether in hexanes

实验过程

To a solution of 2-tert-butyldimethylsilyloxymethyl-4-trimethylacetyloxybromobenzene (48 g) in dry dimethylformamide (460 ml) is added bis(triphenylphosphine)palladium dichloride (2.5 g). The resulting solution is degassed and dry triethylamine (67 ml) added, followed by methyl acrylate (42.6 ml). The resulting solution is stirred at 135° C. for about 1 hour, cooled, diluted with ether, washed with water, dried over magnesium sulfate, filtered, then concentrated under reduced pressure. The residue is purified by flash chromatography, eluting with 10% ether in hexanes, to give the desired product.

来源