تفاعل #344050

معادلة التفاعل

rac-6-acetyloxy-2-ethynyl-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran

3-bromobenzothiophene

triphenylphosphine

triethylamine

→

title compound

rac-6-Acetyloxy-2-[(benzo[b]thiophen-3-yl)ethynyl]-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran

المذيبات

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىdegased by a stream of argon for 15 minutes
2. 2
   workup.ADDITIONPalladium acetate, 30 mg, was then added
3. 3
   أخرىThe reaction mixture was partitioned between saturated sodium bicarbonate solution and toluene
4. 4
   غسيلThe organic phase was washed with water
5. 5
   أخرىdried
6. 6
   أخرىevaporated
7. 7
   أخرىThe residue was chromatographed over 50 g of silica gel
8. 8
   غسيلfor elution
9. 9
   أخرىThe combined clean fractions were crystallized from hexane

الإجراء التجريبي

A mixture of 0.544 g of rac-6-acetyloxy-2-ethynyl-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran, 0.64 g of 3-bromobenzothiophene, 90 mg of triphenylphosphine, 20 mg of cuprous iodide, 2 ml of triethylamine and 40 ml of dimethylformamide was stirred and degased by a stream of argon for 15 minutes. Palladium acetate, 30 mg, was then added and the mixture was heated at 95° C. for 5 hours. The reaction mixture was partitioned between saturated sodium bicarbonate solution and toluene. The organic phase was washed with water, dried and evaporated. The residue was chromatographed over 50 g of silica gel using toluene for elution. The combined clean fractions were crystallized from hexane to give the title compound with m.p. 96°-99°.

المصدر