تفاعل #73048

معادلة التفاعل

tetrahydro-4H-thiopyran-4-one

nitromethane

→

4-(nitromethyl)tetrahydro-2H-thiopyran-4-ol

المردود 42.7%

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   تركيزconcentrated under reduced pressure
2. 2
   أخرىThe residue was partitioned between chloroform (400 mL) and water (60 mL)
3. 3
   استخلاصThe aqueous was extracted with chloroform (5×100 mL)
4. 4
   تجفيفThe combined organics were dried over magnesium sulfate
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated under reduced pressure
7. 7
   أخرىThe residue was purified by HPFC
8. 8
   غسيلeluting with a gradient of 3-35% ethyl acetate in hexanes

الإجراء التجريبي

Under a nitrogen atmosphere sodium methoxide (1.03 mL of 25 wt % in methanol, 4.51 mmol) was added dropwise to a solution of tetrahydro-4H-thiopyran-4-one (10.48 g, 90.20 mol) and nitromethane (7.33 mL, 135.3 mmol) in ethanol (6 mL). The reaction mixture was stirred at ambient temperature for 5 days and then concentrated under reduced pressure. The residue was partitioned between chloroform (400 mL) and water (60 mL). The aqueous was extracted with chloroform (5×100 mL). The combined organics were dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was purified by HPFC eluting with a gradient of 3-35% ethyl acetate in hexanes to provide 10.23 g of 4-(nitromethyl)tetrahydro-2H-thiopyran-4-ol.

المصدر