Sodium hydride → 5,5-dimethyl-3-(2,2-dimethylpropyloxy)-4-(4-(methylsulfonyl)phenyl)-5H-furan-2-one

HRID 565111Notes

Reaction equation

HRID 565111 reaction equation
[CH3:1][C:2]1([CH3:19])[O:6][C:5](=[O:7])[C:4]([OH:8])=[C:3]1[C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=1.[H-].[Na+].[CH2:22](I)[C:23]([CH3:26])([CH3:25])[CH3:24]>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1([CH3:19])[O:6][C:5](=[O:7])[C:4]([O:8][CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[C:3]1[C:9]1[CH:10]=[CH:11][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 84953Propane, 1-iodo-2,2-dimethyl-HCID 155422043-Hydroxy-5,5-dimethyl-4-[4-(methylsulfonyl)phenyl]-2(5H)-furanone

Product 1

HCID 219484215,5-dimethyl-3-(2,2-dimethylpropyloxy)-4-(4-(methylsulfonyl)phenyl)-5H-furan-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5,5-dimethyl-3-hydroxy-4-(4-(methylsulfonyl)phenyl)-5H-furan-2-one (500 mg, 1.77 mmol, Example 109, Step 1) in DMF (6 mL) were added NaH (65 mg, 1.2 eq.), and neopentyl iodide (585 μL). After a period of 18 h at 70° C., the reaction mixture was diluted with EtOAc. The mixture was washed with H2O and the organic phase separated, dried over MgSO4 and evaporated under reduced pressure. The resulting oil was purified by flash chromatography to provide the title compound (124 mg) as a white solid after precipitation with Et2O.

Workup

  1. washThe mixture was washed with H2O
  2. customthe organic phase separated
  3. dry with materialdried over MgSO4
  4. customevaporated under reduced pressure
  5. customThe resulting oil was purified by flash chromatography

Sources & evidence

ORD record
ord-b3063fa9e1234cbea09ad10c324ba3be
Source dataset
uspto-grants-2001_01
Patent number
US06169188A

Reaction notes

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