Pyridine → 5,5-Dimethyl-4-(4-(methylsulfonyl)phenyl)-3-(4-methoxyphenyl)-2-(5H)-furanone

HRID 325178Notes

Reaction equation

HRID 325178 reaction equation
[OH:1][C:2]([CH3:16])([CH3:15])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)=O.N1C=CC=CC=1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32](Cl)=[O:33])=[CH:27][CH:26]=1.C1CCN2C(=NCCC2)CC1>C(Cl)Cl.CCOC(C)=O.Cl>[CH3:15][C:2]1([CH3:16])[O:1][C:32](=[O:33])[C:31]([C:28]2[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)=[C:3]1[C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27346884-Methoxyphenylacetyl chlorideHCID 154285142-Hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one

Product 1

HCID 155167095,5-Dimethyl-4-(4-(methylsulfonyl)phenyl)-3-(4-methoxyphenyl)-2-(5H)-furanone

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cold solution (0° C.) of 2-hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)-propane-1-one (726 mg, 3.5 mmol, Step 3), pyridine (0.5 mL, 6.2 mmol) in CH2Cl2 (10 mL) was added 4-methoxyphenylacetyl chloride (1.5 g, 8.4 mmol) over 2 minutes. The resulting yellow solution was stirred at r.t. for 18 h. Then DBU was added in portions every 30 min. (3×1.0 mL, 3×6.7 mmol). The reaction was diluted with EtOAc (100 mL) and 1N HCl (50 mL). The organic layer was washed with water (50 mL), dried over MgSO4 and concentrated. The crude product was purified first by flash chromatography eluted with 40% EtOAc in hexane and then by crystallization in EtOAc and hexane (1:1, 26 mL) to give the title compound as a white solid.

Workup

  1. washThe organic layer was washed with water (50 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified first by flash chromatography
  5. washeluted with 40% EtOAc in hexane
  6. customby crystallization in EtOAc

Sources & evidence

ORD record
ord-8ff12c79c6c343788b1af6fba6af283c
Source dataset
uspto-grants-2001_04
Patent number
US06222048B1

Reaction notes

Loading…