HCID 59609970, compound → HCID 44180852, compound

HRID 1042032Notes

Reaction equation

HRID 1042032 reaction equation
[OH:1][C:2]1[C:7]([C:8](=[O:18])[CH2:9][C:10]([CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=O)=[CH:6][CH:5]=[CH:4][C:3]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>[Cu](Cl)Cl.C(O)C>[C:19]1([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]3[C:2]=2[O:1][C:10]([CH:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[CH:9][C:8]3=[O:18])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 59609970HCID 59609970, compound

Product 1

HCID 44180852HCID 44180852, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

A 5 mL microwave vial was charged with a magnetic stirring bar, crude 1-(2-hydroxybiphenyl-3-yl)-3-(tetrahydro-2H-pyran-4-yl)propane-1,3-dione (320 mg, 1 mmol), ethanol (3 mL), and copper (II) chloride (13 mg, 0.1 mmol). The reaction vial was sealed, the reaction mixture magnetically stirred and heated via microwave irradiation to 140° C. for 10 minutes. The resulting solution was concentrated in vacuo and purified by high-pressure liquid chromatography to give 8-phenyl-2-(tetrahydro-2H-pyran-4-yl)-4H-chromen-4-one (67).

Workup

  1. additionA 5 mL microwave vial was charged with a magnetic stirring bar
  2. customThe reaction vial was sealed
  3. concentrationThe resulting solution was concentrated in vacuo
  4. custompurified by high-pressure liquid chromatography

Sources & evidence

ORD record
ord-2476fd5c1bc54b4e8f99ed61be189f97
Source dataset
uspto-grants-2013_10
Patent number
US08557807B2

Reaction notes

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