Water → 6-[2-(tetrahydropyran-2-yloxy)ethyl]-6H-furo[2,3-c]pyridin-7-one

HRID 1183077Notes

Reaction equation

[H-].[Na+].[O:3]1[C:7]2[C:8](=[O:12])[NH:9][CH:10]=[CH:11][C:6]=2[CH:5]=[CH:4]1.I[CH2:14][CH2:15][O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1.O>CN(C=O)C.C(OCC)(=O)C>[O:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]1[O:16][CH2:15][CH2:14][N:9]1[CH:10]=[CH:11][C:6]2[CH:5]=[CH:4][O:3][C:7]=2[C:8]1=[O:12]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (60% in oil, 138 mg, 3.5 mmol) was suspended in DMF (10 ml). A DMF solution (5 ml) of 6H-furo[2,3-c]pyridin-7-one (310 mg, 2.3 mmol) was added thereto at 0° C., and stirring was conducted at the same temperature for 1 hour. A DMF solution (5 ml) of 2-(2-iodoethoxy)tetrahydropyran (1175 mg, 4.6 mmol) was added thereto, and stirring was conducted at room temperature overnight. Water was added to the reaction mixture and extraction with ethyl acetate was performed. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1→1:1). The purified product was concentrated under reduced pressure to thereby obtain 450 mg (yield: 74%) of 6-[2-(tetrahydropyran-2-yloxy)ethyl]-6H-furo[2,3-c]pyridin-7-one as a yellow oil.

Workup

stirringstirring
waitwas conducted at room temperature overnight
washThe organic layer was washed with water
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1→1:1)
concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record: ord-71cc963258034de7aae014b14b2f4354
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664217B2

Reaction notes

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