Sodium hydride → 5-(4'-Methyl-biphenyl-4-yloxymethyl)-furan-2-carboxylic acid ethyl ester

HRID 899517Notes

Reaction equation

HRID 899517 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH2:17]([O:19][C:20]([C:22]1[O:23][C:24]([CH2:27]Cl)=[CH:25][CH:26]=1)=[O:21])[CH3:18]>CN(C)C=O>[CH2:17]([O:19][C:20]([C:22]1[O:23][C:24]([CH2:27][O:14][C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)=[CH:9][CH:10]=2)=[CH:25][CH:26]=1)=[O:21])[CH3:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylateHCID 13827894-(4-Methylphenyl)phenol2×

Product 1

HCID 596949875-(4'-Methyl-biphenyl-4-yloxymethyl)-furan-2-carboxylic acid ethyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-5 °C

Procedure

4′-Methyl-biphenyl-4-ol (Intermediate 5; 2.0 g, 10.9 mmol) was added to a suspension of sodium hydride (60% dispersion; 384 mg, 9.6 mmol) in N,N-dimethylformamide (30 mL) and the mixture was stirred at −5° C. for 20 min. A solution of 5-(chloro-methyl)-furan-2-carboxylic acid ethyl ester (1.6 g, 8.5 mmol) in N,N-dimethylformamide (60 mL) was added and the reaction mixture was stirred overnight at room temperature. The solvents were evaporated under reduced pressure and the residue was partitioned between water and ethyl acetate. The aqueous layer was extracted twice with ethyl acetate, and the combined organic layers were washed with water and brine, dried (sodium sulfate), filtered, evaporated, and chromatographed, eluting with 0-50% methylene chloride/hexanes to give 5-(4′-methyl-biphenyl-4-yloxymethyl)-furan-2-carboxylic acid ethyl ester (2.4 g, 84%).

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. customThe solvents were evaporated under reduced pressure
  3. customthe residue was partitioned between water and ethyl acetate
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. washthe combined organic layers were washed with water and brine
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. customevaporated
  9. customchromatographed
  10. washeluting with 0-50% methylene chloride/hexanes

Sources & evidence

ORD record
ord-070b58dd4be345a09222170e6b866c5e
Source dataset
uspto-grants-2008_04
Patent number
US07355049B2

Reaction notes

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