Potassium Carbonate → HCID 18446016, compound

HRID 460546Notes

Reaction equation

HRID 460546 reaction equation
[OH:1][C:2]1[C:10]2[CH:9]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:19][C@H:20]1[O:22][CH2:21]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:19]([O:1][C:2]1[C:10]2[CH:9]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)[C@H:20]1[O:22][CH2:21]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10868995(S)-(+)-Glycidyl-4-nitrobenzoateHCID 14494065Methyl 4-hydroxybenzofuran-2-carboxylate

Product 1

HCID 18446016HCID 18446016, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution (60 ml) of methyl 4-hydroxybenzo(b)furan-2-carboxylate (3.6 g) in DMF were added (S)-glycidyl nosylate (5.1 g) and potassium carbonate (6.5 g) and the mixture was stirred at room temperature for 8 hr. The reaction mixture was concentrated under reduced pressure and ethyl acetate was added to the residue. The mixture was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (4.1 g) as a yellow crystalline compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and ethyl acetate
  2. additionwas added to the residue
  3. washThe mixture was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9ce58651bbb2473997b778ccb0267d73
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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