تفاعل #57598

معادلة التفاعل

3-methyl-4-trifluoromethanesulfonyloxy-benzofuran-2-carboxylic acid ethyl ester

vinyl tributyltin

lithium chloride

→

3-methyl-4-vinylbenzofuran-2-carboxylic acid ethyl ester

المردود 75.2%

المذيبات

DMF

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled to room temperature
2. 2
   استخلاصextracted with ether
3. 3
   غسيلThe combined organics were washed with water and brine
4. 4
   تجفيفdried over magnesium sulfate
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:25)

الإجراء التجريبي

To a solution of 2.48 g (7.05 mmol) of 3-methyl-4-trifluoromethanesulfonyloxy-benzofuran-2-carboxylic acid ethyl ester (Example 20, Step 2) in 30 mL of DMF was added 2.16 mL (7.40 mmol) of vinyl tributyltin, 0.898 g (21.1 mmol) of lithium chloride and 0.247 g (0.352 mmol) of tetrakis(triphenylphosphine)palladium(0). The reaction was heated to 90° C. for 3 h and then cooled to room temperature. The reaction was diluted with water and extracted with ether. The combined organics were washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:25) to provide 1.22 g of 3-methyl-4-vinylbenzofuran-2-carboxylic acid ethyl ester.

المصدر