تفاعل #168194

معادلة التفاعل

Sodium hydride

ethanol

methyl cyclopentanecarboxylate

1-(4-methoxyphenyl)ethanone

→

1-cyclopentyl-3-(4-methoxyphenyl)propane-1,3-dione

المردود 56.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was heated
2. 2
   درجة الحرارةto reflux for 11 h
3. 3
   أخرىquenched with water (100 mL)
4. 4
   أخرىThe THF solvent was evaporated in vacuo
5. 5
   استخلاصThe residue was extracted with ethyl acetate (3×100 mL)
6. 6
   غسيلThe combined extracts were washed with brine (25 mL)
7. 7
   تجفيفdried (MgSO4)
8. 8
   تركيزconcentrated
9. 9
   غسيلeluting with 0-15% ethyl acetate in hexanes

الإجراء التجريبي

Sodium hydride (1.378 g, 59.9 mmol, 60% suspension in mineral oil) and ethanol (2.0 mL) were added to a solution of methyl cyclopentanecarboxylate (6.14 g, 47.9 mmol) and 1-(4-methoxyphenyl)ethanone (6.00 g, 40.0 mmol) in THF (200 mL). The mixture was heated to reflux for 11 h, quenched with water (100 mL) and acidified to pH˜2 with 1 N HCl. The THF solvent was evaporated in vacuo. The residue was extracted with ethyl acetate (3×100 mL). The combined extracts were washed with brine (25 mL), dried (MgSO4) and concentrated. Silica gel chromatography, loading with hexanes and small amount of toluene and eluting with 0-15% ethyl acetate in hexanes, gave 1-cyclopentyl-3-(4-methoxyphenyl)propane-1,3-dione as yellow liquid (5.494 g, 56% yield). MS (ES+) m/z: 247 (M+H); LC retention time: 4.510 and 3.578 min, likely a mixture of keto and enol forms (analytical HPLC Method A).

المصدر