반응 #1985938

반응 방정식

2-tert-butyldimethylsilyloxymethyl-4-trimethylacetyloxybromobenzene

→

desired product

Methyl 2-Tert-butyldimethylsilyloxymethyl-4-trimethylacetyloxycinnamate

용매

dimethylformamide

반응 조건

후처리

1. 1
   기타The resulting solution is degassed
2. 2
   workup.ADDITIONdry triethylamine (67 ml) added
3. 3
   온도cooled
4. 4
   workup.ADDITIONdiluted with ether
5. 5
   세척washed with water
6. 6
   건조dried over magnesium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated under reduced pressure
9. 9
   기타The residue is purified by flash chromatography
10. 10
    세척eluting with 10% ether in hexanes

실험 절차

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.

출처