Potassium Carbonate → HCID 10634805, compound

HRID 2061345Notes

Reaction equation

HRID 2061345 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:17]([O:19][CH:20]([O:23][CH2:24][CH3:25])[CH2:21]Br)[CH3:18]>CN(C=O)C>[CH2:17]([O:19][CH:20]([O:23][CH2:24][CH3:25])[CH2:21][O:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH:4]=[O:5])[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 27373285-Fluorosalicylaldehyde

Product 1

HCID 10634805HCID 10634805, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension containing 2-hydroxy-5-fluorobenzaldehyde (500 mg, 3.57 mmol) and K2CO3 (524 mg, 13.79 mmol) in DMF (10 mL), bromoacetaldehyde diethyl acetal (0.6 mL, 3.93 mmol) was added dropwise. The mixture was refluxed for 4 h. After cooling, the precipitate was filtered off and the solvent was evaporated in vacuo. The crude residue was adsorbed on silica gel and purified by flash chromatography, eluting with hexane/EtOAc (4:1) to give 12 (300 mg, 33%) as an oil. 1H NMR (500 MHz, CDCl3): δ: 10.30 (1H, s, CHO), 7.31 (1H, d, J=7.85 Hz), 7.10 (1H, t, J=7.80 Hz), 6.87 (1H, d, J=8.86 Hz), 4.75 (1H, s, CH), 3.97 (2H, d, J=2.35 Hz, CH2), 3.67-3.64 (2H, m, CH2CH3), 3.53-3.50 (2H, m, CH2CH3), 1.11 (6H, t, J=6.00 Hz, 2×CH3).

Workup

  1. additionwas added dropwise
  2. temperatureThe mixture was refluxed for 4 h
  3. temperatureAfter cooling
  4. filtrationthe precipitate was filtered off
  5. customthe solvent was evaporated in vacuo
  6. custompurified by flash chromatography
  7. washeluting with hexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-e79082e4868b472cbf85fa567661f3f2
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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