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

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.

1. concentrationconcentrated under reduced pressure
2. customThe residue was partitioned between chloroform (400 mL) and water (60 mL)
3. extractionThe aqueous was extracted with chloroform (5×100 mL)
4. dry with materialThe combined organics were dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by HPFC
8. washeluting with a gradient of 3-35% ethyl acetate in hexanes

ORDレコード

ord-a8faff76167a49a6a932dbb483511e5f

出典データセット

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08541438B2