Isopropyl iodide → 5,5-Dimethyl-3-(1-methylethoxy)-4-(4-(methylsulfonyl)phenyl)-2(5H)-furanone

HRID 565106Notes

Reaction equation

HRID 565106 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.I[CH:21]([CH3:23])[CH3:22]>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:19])[O:6][C:5](=[O:7])[C:4]([O:8][CH:21]([CH3:23])[CH3:22])=[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

4

Reactant 2

HCID 6362Isopropyl iodideHCID 155422043-Hydroxy-5,5-dimethyl-4-[4-(methylsulfonyl)phenyl]-2(5H)-furanone

Product 1

HCID 98402375,5-Dimethyl-3-(1-methylethoxy)-4-(4-(methylsulfonyl)phenyl)-2(5H)-furanone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of the alcohol of Step 1 (100 mg, 0.354 mmol) in benzene (5.0 mL) were added an excess of 2-iodopropane (105 mL) and Ag2CO3 (294 mg, 1.06 mmol). After a period of 18 h at 45° C., the reaction mixture was filtered over celite and washed with CH2CL2. After evaporation, the crude compound was purified by flash chromatography (35% to 40% EtOAc) to provide 70 mg of the title compound.

Workup

  1. filtrationthe reaction mixture was filtered over celite
  2. washwashed with CH2CL2
  3. customAfter evaporation
  4. customthe crude compound was purified by flash chromatography (35% to 40% EtOAc)

Sources & evidence

ORD record
ord-f644c5853575452f92a7d3d65fbce9bd
Source dataset
uspto-grants-2001_01
Patent number
US06169188A

Reaction notes

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