تفاعل #1985938

معادلة التفاعل

2-tert-butyldimethylsilyloxymethyl-4-trimethylacetyloxybromobenzene

→

desired product

Methyl 2-Tert-butyldimethylsilyloxymethyl-4-trimethylacetyloxycinnamate

المذيبات

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىThe resulting solution is degassed
2. 2
   workup.ADDITIONdry triethylamine (67 ml) added
3. 3
   درجة الحرارةcooled
4. 4
   workup.ADDITIONdiluted with ether
5. 5
   غسيلwashed with water
6. 6
   تجفيفdried over magnesium sulfate
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated under reduced pressure
9. 9
   أخرىThe residue is purified by flash chromatography
10. 10
    غسيلeluting with 10% ether in hexanes

الإجراء التجريبي

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.

المصدر