Potassium Carbonate → HCID 58951921, compound

HRID 1694793

Reaction equation

HRID 1694793 reaction equation
[OH:1][C:2]1[C:9]([CH:10]=O)=[CH:8][C:7]([CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].Br[CH:20](C(OCC)=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>CN(C=O)C>[CH2:24]([O:23][C:21]([C:20]1[O:1][C:2]2[C:3]([CH:4]=[O:5])=[CH:6][C:7]([CH3:12])=[CH:8][C:9]=2[CH:10]=1)=[O:22])[CH3:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69637Diethyl bromomalonateHCID 817442,6-Diformyl-4-methylphenol

Product 1

HCID 58951921HCID 58951921, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-hydroxy-5-methylisophtalaldehyde (1 g) in DMF (10 ml) was treated under an Argon atmorphere with potassium carbonate (1.01 g) and diethyl bromomalonate (1.60 g). The reaction mixture was heated to 100° C. for 20 hrs, then cooled to r.t., quenched with water and extracted with EtOAc. The organics were dried over MgSO4, filtrated and concentrated to obtain 7-formyl-5-methyl-benzofuran-2-carboxylic acid ethyl ester (1.34 g) as off-white solid. MS (ISP): 233.1 ((M+H)+.). The crude product was used in the next reaction step without further purification.

Workup

  1. temperaturecooled to r.t.
  2. customquenched with water
  3. extractionextracted with EtOAc
  4. dry with materialThe organics were dried over MgSO4
  5. filtrationfiltrated
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-58a6c1d77a5a4d58bdb1ebdd7c541ccf
Source dataset
uspto-grants-2012_04
Patent number
US08158668B2

Linked notes

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