تفاعل #6657

معادلة التفاعل

2,2,4,4-tetramethyl-6-ethynylchroman

Compound 5

2,2,4,4-tetramethyl-6-ethynylchroman

ethyl 6-chloronicotinate

Compound 98

ethyl 6-chloronicotinate

→

title compound

Ethyl 6-[(2,2,4,4-tetramethylchroman-6-yl)-ethynyl]nicotinate

المذيبات

triethylamine

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled to room temperature
2. 2
   أخرىThe triethylamine was then removed under vacuum
3. 3
   أخرىthe residue purified by flash chromatography (silica; 5% ethyl acetate in hexanes)

الإجراء التجريبي

A solution of 233 mg (1.09 mmol) of 2,2,4,4-tetramethyl-6-ethynylchroman (Compound 5) and 209 mg (1.09 mmol) of ethyl 6-chloronicotinate (Compound 98) in 1 ml of triethylamine was degassed and then treated under argon with a powdered mixture of 50 mg (0.26 mmol) of cuprous iodide and 100 mg (0.14 mmol) of bis(triphenylphosphine) palladium (II) chloride. The reaction mixture was heated under argon at 55 degrees C. for 80 h and then cooled to room temperature. The triethylamine was then removed under vacuum and the residue purified by flash chromatography (silica; 5% ethyl acetate in hexanes) to give the title compound as a yellow oil. PMR (CDCl3): δ 1.36 (12H, s), 1.42 (3H, t, J~7.2 Hz), 1.85 (2H, s), 4.37 (2H, q, J~7.2 Hz), 6.79 (1H, d, J~.4 Hz), 7.34 (1 H, dd, J~2.1 Hz), 7.56 (1H, d, J~8.7 Hz), 7.60 (1H, d, J~2.1 Hz), 8.27 (1H, dd, J~8.7 Hz, 2.4 Hz), 9.19 (1H, d, J~2.4 Hz). MS exact masss, m/e 363.1837 (calcd. for C23H25O3N, 363.1834).

المصدر