Sulfolane → HCID 59202238, compound

HRID 1685818Notes

Reaction equation

HRID 1685818 reaction equation
[S:1]1(=[O:7])(=[O:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li])CCC.[CH:13]([C:15]1[CH:20]=[CH:19][C:18]([CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17][CH:16]=1)=[O:14]>O1CCCC1.CCCCCC>[O:6]=[S:1]1(=[O:7])[CH2:5][CH2:4][CH2:3][CH:2]1[CH:13]([OH:14])[C:15]1[CH:16]=[CH:17][C:18]([CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 31347SulfolaneHCID 13066570rac 2-(4-Formylphenyl)propionic Acid Ethyl EsterHCID 178418339Butyllithium

Product 1

HCID 59202238HCID 59202238, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

Tetrahydrothiophene-1,1-dioxide (1.5 g) was dissolved in tetrahydrofuran (10 ml), and to the solution was added dropwise a 1.6 M solution of n-butyllithium in hexane (6.0 ml) at −60° C. The reaction mixture was gradually warmed to 0° C., stirred at the same temperature for 30 minutes, then a solution of ethyl 2-(4-formylphenyl)propionate (1.5 g) in tetrahydrofuran (2.0 ml) was added dropwise at 0° C., and the mixture was stirred at room temperature for 2 days. The reaction mixture was quenched with 10% aqueous citric acid, and then extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to give the title compound (800 mg, 39%).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 days
  2. customThe reaction mixture was quenched with 10% aqueous citric acid
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-45968a0f8ddc436eb946993cd0f06cc7
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

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