Ethanol → HCID 135432621, compound

HRID 982862Notes

Reaction equation

HRID 982862 reaction equation
[C:1]([C:4]1[C:5](=[O:12])[O:6][C:7]([CH3:11])=[CH:8][C:9]=1[OH:10])(=[O:3])[CH3:2].[CH3:13][O:14][C:15]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:16]=1[CH:17]=O.C(O)C.N1CCCCC1>C(Cl)Cl.C(OCC)(=O)C.CC(C)=O.CCCCCC.C(OCC)(=O)C>[CH3:13][O:14][C:15]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:16]=1[CH:17]=[CH:2][C:1]([C:4]1[C:5](=[O:12])[O:6][C:7]([CH3:11])=[CH:8][C:9]=1[OH:10])=[O:3]

Participants

7

Reactant 4

HCID 702EthanolHCID 8082PiperidineHCID 691752,4-DimethoxybenzaldehydeHCID 546784943-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one

Product 1

HCID 135432621HCID 135432621, compound

Reagents, catalysts & solvents 2

HCID 20450765HCID 20450765, compoundSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

3-Acetyl-4-hydroxy-6-methyl-pyran-2-one (5.07 g, 30.15 mmol) and 2,4-dimethoxybenzaldehyde (5.03 g, 30.27 mmol) were combined in a 250 mL round bottom flask. Absolute ethanol (20 mL) and piperidine (0.10 eq, 0.30 mL, 3.0 mmol) were added and the mixture heated to between 80 and 85 ° C. The reaction was monitored by TLC (silica gel, hexane-ethyl acetate (1:1 v/v) and methylene chloride-ethyl acetate-acetone (5:5:1 v/v)) and analytical HPLC. After 20 hours (>95% completion) the reaction mixture was cooled to room temperature to provide 3-[3-(2,4-dimethoxy-phenyl)-acryloyl]-4-hydroxy-6-methyl-pyran-2-one as a bright orange crystalline precipitate. MS M+317. NMR (CDCl3-TMS): d 8.31 (m, 2H), 7.69 (d, 1H, J=9 Hz), 6.54 (d, 1H, J=9 Hz), 6.45 (s, 1H), 5.93 (s, 1H), 3.91 (s, 3H), 3.87 (s, 3H), 2.26 (s, 3H) NMR (DMSO-d6): d 8.11 (s, 2H), 7.62 (d, 1H, J=9 Hz), 6.63 (bs, 2H), 6.23 (s, 1H), 3.87 (s, 3H), 3.82 (s, 3H), 2.28 (s, 3H).

Workup

  1. temperaturethe mixture heated to between 80 and 85 ° C

Sources & evidence

ORD record
ord-9da26ddd68f348ef9b425329616c47b9
Source dataset
uspto-grants-2005_03
Patent number
US06861419B2

Reaction notes

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