4H-pyran-4-one → 4-Methylbenzaldehyde

HRID 2406408

Reaction equation

O1C=CC(=O)C=C1.[S].[O:9]=[C:10]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)CC#N.N1CCOCC1>C(O)C>[C:17]1([CH3:20])[CH:18]=[CH:19][C:14]([CH:10]=[O:9])=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 40 °C

Procedure

4-Pyranone (2.31 mL, 24.97 mmol) and sulphur (801 mg, 24.97 mmol) were added to a solution of 3-oxo-3-p-tolyl-propionitrile (3.79 g, 23.8 mmol) in ethanol (40 mL) followed by morpholine (2.18 mL, 24.97 mmol) and the reaction heated at 40° C. for 16 hours, The reaction mixture was concentrated in vacuo and the residue purified by flash chromatography on silica eluting with 0-20% ethylacetate/heptanes to afford 12-Amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3-yl)-p-tolyl-methanone as a yellow solid (2.2 g, 36% yield). LCMS (2 min acidic) 1.07 min ES+/AP+ 274 (MH+). 1HNMR (400 MHz, CDCl3) δ ppm 2.00-2.03 (m, 2H), 2.42 (s, 3H), 3.80-3.84 (m, 2H), 4.80 (s, 2H), 6.60 (br s, 2H), 7.20 (d, 2H), 7.41 (d, 2H).

Workup

concentrationThe reaction mixture was concentrated in vacuo
customthe residue purified by flash chromatography on silica eluting with 0-20% ethylacetate/heptanes

Sources & evidence

ORD record: ord-137b9c2d900f476f9a9343f506ac1196
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809363B2

Linked notes

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