反応 #1985938

反応方程式

2-tert-butyldimethylsilyloxymethyl-4-trimethylacetyloxybromobenzene

→

desired product

Methyl 2-Tert-butyldimethylsilyloxymethyl-4-trimethylacetyloxycinnamate

溶媒

dimethylformamide

反応条件

後処理

1. 1
   その他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
   洗浄washed with water
6. 6
   乾燥dried over magnesium sulfate
7. 7
   ろ過filtered
8. 8
   濃縮concentrated under reduced pressure
9. 9
   その他The residue is purified by flash chromatography
10. 10
    洗浄eluting with 10% ether in hexanes

実験手順

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.

出典