Dimethyl Sulfoxide → Methyl 5-(4-hydroxytetrahydrofuran-3-yloxy)-4'-methylbiphenyl-3-carboxylate

HRID 1845325Notes

Reaction equation

HRID 1845325 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O.[CH:29]12[O:34][CH:33]1[CH2:32][O:31][CH2:30]2>CCOC(C)=O>[OH:34][CH:29]1[CH2:30][O:31][CH2:32][CH:33]1[O:1][C:2]1[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 675113,6-Dioxabicyclo[3.1.0]hexaneHCID 58187967Methyl 5-hydroxy-4'-methyl-[1,1'-biphenyl]-3-carboxylate

Product 1

HCID 58188331Methyl 5-(4-hydroxytetrahydrofuran-3-yloxy)-4'-methylbiphenyl-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A stirred mixture of methyl 5-hydroxy-4′-methylbiphenyl-3-carboxylate (370 mg, 1.4 mmol), potassium carbonate (421 mg, 3.05 mmol), DMSO (8 mL), and 3,6-dioxabicyclo[3.1.0]hexane (260 mg, 3.0 mmol) was heated at 110° C. overnight. After cooling, the reaction mixture was diluted with EtOAc. The organic phase was washed with aq. NaHCO3 (sat.), dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by flash chromatography to afford the title compound.

Workup

  1. temperatureAfter cooling
  2. washThe organic phase was washed with aq. NaHCO3 (sat.)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-97cc728651fb49dcb451a4f899c04298
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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