Potassium Carbonate → HCID 18446016, compound

HRID 2085118Notes

Reaction equation

HRID 2085118 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-5653825d20044d41a37f8fab59b92555
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

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