Pyridine → HCID 58712145, compound

HRID 1909443Notes

Reaction equation

HRID 1909443 reaction equation
[CH2:1]([C:3]1[C:4]([OH:23])=[CH:5][C:6]([OH:22])=[C:7]([C:9](=[O:21])[CH2:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)[CH:8]=1)[CH3:2].N1C=CC=C[CH:25]=1.C(OC)(OC)OC>N1CCCCC1.CCOC(C)=O>[CH2:1]([C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][C:4]=1[OH:23])[O:22][CH:25]=[C:10]([C:11]1[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=1)[C:9]2=[O:21])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 9005Trimethyl orthoformateHCID 58712184HCID 58712184, compound

Product 1

HCID 58712145HCID 58712145, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To 1-(5-ethyl-2,4-dihydroxy-phenyl)-2-naphthalen-2-yl-ethanone (c, 0.50 g) was added a mixture of pyridine (2 mL), trimethyl orthoformate (2 mL) and piperidine (2 drops), and the mixture was heated at 120° C. for 12 h. The mixture was cooled to room temperature, diluted with EtOAc (100 mL) then washed with 1 N HCl (100 mL). The organic layer was washed with water and dried. The oil obtained on concentration of the organic layer was crystallized in EtOAc/hexanes to give 6-ethyl-7-hydroxy-3-naphthalen-2-yl-chromen-4-one (d, 0.36 g).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washthen washed with 1 N HCl (100 mL)
  3. washThe organic layer was washed with water
  4. customdried
  5. customThe oil obtained on concentration of the organic layer
  6. customwas crystallized in EtOAc/hexanes

Sources & evidence

ORD record
ord-d589ea03042e415d9b70f3a402cf96b0
Source dataset
uspto-grants-2013_12
Patent number
US08598366B2

Reaction notes

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