3,4-dihydro-2H-pyran → HCID 86651374, compound

HRID 1879549Notes

Reaction equation

HRID 1879549 reaction equation
[OH:1][C:2]1[C:11]([OH:12])=[C:10]2[C:5]([C:6]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:7][C:8](=[O:13])[O:9]2)=[CH:4][CH:3]=1.[O:20]1[CH:25]=[CH:24][CH2:23][CH2:22][CH2:21]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1COCC1.C(Cl)Cl.CCOC(C)=O>[OH:12][C:11]1[C:2]([O:1][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25][O:20]2)=[CH:3][CH:4]=[C:5]2[C:10]=1[O:9][C:8](=[O:13])[CH:7]=[C:6]2[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 54130347,8-dihydroxy-4-phenyl-2H-chromen-2-one

Product 1

HCID 86651374HCID 86651374, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 7,8-dihydroxy-4-phenyl-2H-chromen-2-one (500 mg, 2 mmol) and 3,4-dihydro-2H-pyran in 4 mL THF and 4 mL DCM was added pyridinium paratoluene sulfonate (PPTS, 8 mg). The mixture was stirred at rt for 15 h under Ar atmosphere and diluted with EtOAc (50 mL). It was washed with NaHCO3 (sat. 30 mL) and water (50 mL) and dried over MgSO4 and concentrated under reduced pressure. The residue was chromatographed (hexane/EtOAc) to afford 8-hydroxy-4-phenyl-7-(tetrahydro-2H-pyran-2-yloxy)-2H-chromen-2-one as a yellow solid (180 mg, 26%). MS (ESI) m/z 339 (M+H+).

Workup

  1. washIt was washed with NaHCO3 (sat. 30 mL) and water (50 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was chromatographed (hexane/EtOAc)

Sources & evidence

ORD record
ord-a043a9903f214d5cbcca0d910a42db5b
Source dataset
uspto-grants-2012_11
Patent number
US08318132B2

Reaction notes

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