Ammonium Hydroxide → Oxane-4-carboxamide

Ammonium hydroxide (1 L) was added to a solution of methyl tetrahydro-2H-pyran-4-carboxylate (20 mL, 150 mmol) in methanol (500 mL), and the reaction was stirred overnight at ambient temperature. Additional ammonium hydroxide (500 mL) was added, and the reaction was stirred for four additional days. The methanol was removed under reduced pressure. Solid sodium chloride was added to the aqueous layer, which was extracted with chloroform (3×150 mL). The combined extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 11.4 g of tetrahydro-2H-pyran-4-carboxamide as a white solid.

1. stirringthe reaction was stirred for four additional days
2. customThe methanol was removed under reduced pressure
3. additionSolid sodium chloride was added to the aqueous layer, which
4. extractionwas extracted with chloroform (3×150 mL)
5. dry with materialThe combined extracts were dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure

ORD record

ord-cc63cef9569b4f0abae5415e1aefe905

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08263594B2