Potassium Carbonate → HCID 21838027, compound

HRID 1740294Notes

Reaction equation

HRID 1740294 reaction equation
P(Cl)(Cl)(Cl)=O.[O:6]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([O:16][CH3:17])=[O:15])=[CH:7]1.[C:21](=O)([O-])[O-:22].[K+].[K+]>CN(C)C=O>[CH:21]([C:7]1[O:6][CH:10]=[CH:9][C:8]=1[C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=1)[C:14]([O:16][CH3:17])=[O:15])=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 21838025Benzoic acid, 3-(3-furanyl)-, methyl ester

Product 1

HCID 21838027HCID 21838027, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N,N-dimethylformamide (1.7 ml) was stirred at 0° C. and to this was added dropwise phosphorus oxychloride (0.51 ml). The mixture was stirred for 30 minutes and was added a solution of methyl 3-(furan-3-yl)benzoate (1 g) in N,N-dimethylformamide (0.6 ml), and then was stirred at room temperature overnight. The reaction mixture was poured onto ice/water and then adjusted to pH 8 with an aqueous potassium carbonate solution. The product was extracted with ethyl acetate-tetrahydrofuran (1:1, 2×100 ml) and the extracts were combined, washed successively with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of hexane:ethyl acetate (5:1) to afford methyl 3-(2-formylfuran-3-yl)benzoate (0.75 g).

Workup

  1. stirringwas stirred at room temperature overnight
  2. additionThe reaction mixture was poured onto ice/water
  3. extractionThe product was extracted with ethyl acetate-tetrahydrofuran (1:1, 2×100 ml)
  4. washwashed successively with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel eluting with a mixture of hexane:ethyl acetate (5:1)

Sources & evidence

ORD record
ord-ccb47575044147f2911927eaf4da5cb7
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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