تفاعل #160338

معادلة التفاعل

5-methyl-[1,3]dioxane-2-carboxylic acid

PPh3

NCS

isopropylamino-5-phenyl-thiophene-2-carboxylic acid methyl ester

→

3-[isopropyl-(5-methyl-[1,3]dioxane-2-carbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester

المردود 35.7%

المذيبات

1,2-dichloroethane

—

hexanes

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction was heated
2. 2
   درجة الحرارةat reflux for 3 days
3. 3
   أخرىThe mixture was evaporated to a residue that
4. 4
   أخرىwas purified by silica gel column chromatography

الإجراء التجريبي

A solution 5-methyl-[1,3]dioxane-2-carboxylic acid (53 mg, 0.47 mmol) in 1,2-dichloroethane at 0° C. was treated with PPh3 (124 mg, 0.47 mmol), NCS (63 mg, 0.47 mmol) and isopropylamino-5-phenyl-thiophene-2-carboxylic acid methyl ester (100 mg, 0.36 mmol). The reaction was heated at reflux for 3 days. The mixture was evaporated to a residue that was purified by silica gel column chromatography using EtOAc:hexanes as eluent to furnished 3-[isopropyl-(5-methyl-[1,3]dioxane-2-carbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (51.8 mg, 35% yield). 1H NMR (CDCl3, 400 MHz): 7.65 (d, 2H), 7.42 (m, 3H), 7.10 (s, 1H), 4.90 (q, 1H), 4.55 (s, 1H), 4.00 (dd, 1H), 3.90 (dd, 1H), 3.85 (s, 3H), 3.10 (t, 1H), 2.95 (t, 1H), 2.10 (m, 1H), 1.25 (d, 3H), 1.05 (d, 3H), 0.58 (d, 3H).

المصدر