反应详情

To a solution of 1-methylcyclohex-3-ene-1-carboxylic acid, 52a, (54.0 g, 385.2 mmol) dissolved in CH2Cl2 (200 mL) was added thionyl chloride (56.2 mL, 770.4 mmol) and 1 mL of DMF. The reaction was warmed to reflux for 3 hrs, then cooled and concentrated in vacuo. The residue was redissolved in 200 mL of CH2Cl2. To the reaction was added ammonium hydroxide (148.2 mL of 13 M solution, 1.9 mol) slowly. The reaction was stirred overnight. The reaction was extracted into CH2Cl2 and water. The organic phase was concentrated in vacuo and purified via flash silica gel chromatography (EtOAc), yielding 25 g of 1-methylcyclohex-3-ene-1-carboxamide.

1. temperatureThe reaction was warmed
2. temperatureto reflux for 3 hrs
3. temperaturecooled
4. concentrationconcentrated in vacuo
5. dissolutionThe residue was redissolved in 200 mL of CH2Cl2
6. extractionThe reaction was extracted into CH2Cl2 and water
7. concentrationThe organic phase was concentrated in vacuo
8. custompurified via flash silica gel chromatography (EtOAc)