Dimethylformamide → HCID 86669349, compound

HRID 924954Notes

Reaction equation

HRID 924954 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:11])[C:9]=1O)[CH:5]=[O:6].I[CH2:13][CH3:14].[C:15]([O-:18])([O-])=O.[K+].[K+].[CH3:21]N(C=O)C>>[CH2:13]([O:11][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([F:1])[C:9]=1[O:18][CH2:15][CH3:21])[CH:5]=[O:6])[CH3:14]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 5936643-Fluoro-4,5-dihydroxybenzaldehyde

Product 1

HCID 86669349HCID 86669349, compoundYield 36.8%

Procedure

To the solution of 3-fluoro-4,5-dihydroxybenzaldehyde (200 mg, 1.28 mmol) in DMF (50 mL) was added iodo-ethane (240 mg, 1.53 mmol) and K2CO3 (210 mg, 1.53 mmol) at 0° C., and the mixture was stirred at room temperature overnight. The reaction mixture was poured into ice-water solution, and extracted with EtOAc. The combined organic layers were washed with brine, dried with Na2SO4, concentrated under reduced pressure, and purified by column chromatography to give 3,4-diethoxy-5-fluorobenzaldehyde (100 mg, 36.8% yield).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-1759b545f77f486abb9b9bce798feb43
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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