تفاعل #160810
ord-de77a11043c949ea9b5f52145eb5ae6a
معادلة التفاعل
الكواشف
ظروف التفاعل
المعالجة
- 1درجة الحرارةrefluxed for 2 hr with a dean-stark trap
- 2workup.DISTILLATIONThe benzene was then distilled off
- 3workup.DISSOLUTIONthe residue was redissolved in THF (2 mL)
- 4workup.ADDITIONwas added
- 5workup.STIRRINGThe reaction mixture was stirred at 0° C. for 2 hr
- 6درجة الحرارةThe mixture was cooled
- 7أخرىquenched with water
- 8استخلاصThe reaction mixture was extracted with diethyl ether (3×20 mL)
- 9غسيلThe combined organic fractions were washed with water and brine (saturated, 100 mL)
- 10أخرىdried
- 11ترشيحfiltered
- 12أخرىthe solvent was evaporated under reduced pressure (400 mmhg)
- 13أخرىThe residue was purified by column chromatography on silica gel
الإجراء التجريبي
Cyclohexylamine (3.43 ml, 30.0 mmol) was added to pyran-3-one (3000 mg, 30.0 mmol) in benzene (20 mL). The reaction mixture was stirred at RT for 30 min and then refluxed for 2 hr with a dean-stark trap. The benzene was then distilled off and the residue was redissolved in THF (2 mL) and added to BuLi (13.18 ml, 33.0 mmol) in THF (Volume: 30.000 ml) at 0° C. The reaction mixture was stirred at 0° C. for 1 h before 5-bromo-1-pentene (5582 mg, 37.5 mmol) was added. The reaction mixture was stirred at 0° C. for 2 hr. The mixture was cooled and quenched with water. The reaction mixture was extracted with diethyl ether (3×20 mL). The combined organic fractions were washed with water and brine (saturated, 100 mL), dried, filtered and the solvent was evaporated under reduced pressure (400 mmhg). The residue was purified by column chromatography on silica gel to provide the title compound. 1H NMR (500 MHz, CDCl3) δ 5.74-5.86 (m, 1H), 4.92-5.06 (m, 2H), 3.90-4.06 (m, 3H), 3.77-3.85 (m, 1H), 2.41-2.49 (m, 1H), 2.16-2.24 (m, 1H), 2.01-2.12 (m, 2H), 1.72-1.97 (m, 2H), 1.31-1.49 (m, 3H).