Monoethyl malonate → 5,5-Dimethyl-4-(4-(methylsulfonyl)phenyl)-2-oxo-2,5-dihydrofuran-3-carboxylic acid ethyl ester

HRID 1106597Notes

Reaction equation

HRID 1106597 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.[C:17]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:18][C:19](O)=[O:20].C1CCN2C(=NCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:24]([O:23][C:17]([C:18]1[C:19](=[O:20])[O:1][C:2]([CH3:16])([CH3:15])[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)=[O:22])[CH3:25]

Participants

6

Reactant 3

HCID 70615Monoethyl malonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 154285142-Hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one

Product 1

HCID 544790785,5-Dimethyl-4-(4-(methylsulfonyl)phenyl)-2-oxo-2,5-dihydrofuran-3-carboxylic acid ethyl esterYield 62.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one (2.87 g, 11.8 mmol), ethyl hydrogen malonate (2.02 g, 15.3 mmol), CMC (6.51 g, 15.4 mmol) and DMAP (0.35 g, 2.8 mmol) was dissolved in 100 mL of CH2Cl2. The mixture was stirred for 14 h at room temperature, then DBU (4 mL, 27 mmol) was added, stirred 1 h, then partitioned between CH2Cl2 and 1M HCl. The organic layer was washed with brine, filtered through cotton an evaporated. Purification by flash chromatography (90% ether/Hex) provided 2.50 g of the title compound.

Workup

  1. stirringstirred 1 h
  2. custompartitioned between CH2Cl2 and 1M HCl
  3. washThe organic layer was washed with brine
  4. filtrationfiltered through cotton an evaporated
  5. customPurification by flash chromatography (90% ether/Hex)

Sources & evidence

ORD record
ord-f32858d5d8dd4471a190a8fbebce5ee9
Source dataset
uspto-grants-2000_05
Patent number
US06057319

Reaction notes

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