Ethyl Acetate → 5,6-Dihydro-3-phenyl-2H-pyran-2-one

HRID 990092Notes

Reaction equation

HRID 990092 reaction equation
Br[C:2]1[C:3](=[O:8])[O:4][CH2:5][CH2:6][CH:7]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[C:9]1([C:2]2[C:3](=[O:8])[O:4][CH2:5][CH2:6][CH:7]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 108560293-bromo-5,6-dihydro-2H-pyran-2-one

Product 1

HCID 184196755,6-Dihydro-3-phenyl-2H-pyran-2-one

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 3-bromo-5,6-dihydropyran-2-one (Org. Syn., 1996, 73, 231) (74.9 g), phenylboronic acid (51.8 g), potassium carbonate (294 g) and tetrakis(triphenylphosphine) palladium(0) (3.4 g) in toluene was heated (100° C.) under an atmosphere of nitrogen for 24 hours. The cooled solution was diluted by addition of ethyl acetate (1000 ml) and water (1000 ml) and the mixture filtered through Hiflo™. The organic phase was dried (MgSO4), evaporated in vacuo and the residue crystallised from methanol and then toluene to give the title compound, 43 g. mp. 100-101° C.

Workup

  1. filtrationthe mixture filtered through Hiflo™
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated in vacuo
  4. customthe residue crystallised from methanol

Sources & evidence

ORD record
ord-e93e874ed850453e897616564fb2d914
Source dataset
uspto-grants-2002_10
Patent number
US06458830B1

Reaction notes

Loading…