Potassium Carbonate → HCID 59603137, compound

HRID 2061350Notes

Reaction equation

HRID 2061350 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:11])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].C([O-])([O-])=O.[K+].[K+].[CH2:18]([O:20][CH:21]([O:24][CH2:25][CH3:26])[CH2:22]Br)[CH3:19]>CN(C=O)C>[CH2:18]([O:20][CH:21]([O:24][CH2:25][CH3:26])[CH2:22][O:10][C:5]1[C:4]([CH3:11])=[CH:3][C:2]([F:1])=[CH:9][C:6]=1[CH:7]=[O:8])[CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 27827485-Fluoro-2-hydroxy-3-methylbenzaldehyde

Product 1

HCID 59603137HCID 59603137, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension containing 5-fluoro-2-hydroxy-3-methylbenzaldehyde (1.0 g, 6.49 mmol) and K2CO3 (980 mg, 7.10 mmol) in DMF (8 mL), bromoacetaldehyde diethyl acetal (1.10 mL, 7.15 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. The product was eluted with hexane/EtOAc (4:1) to give 20 (350 mg, 20%) as an oil, 1H NMR (500 MHz, CDCl3): δ: 10.40 (1H, s, CHO), 7.32 (1H, d, J=7.30 Hz, ArH), 7.14 (1H, d, J=7.75 Hz, ArH), 4.85 (1H, s, CH), 3.95 (2H, s, CH2), 3.75 (2H, t, J=7.15 Hz, CH2CH3), 3.61 (2H, t, J=7.20 Hz, CH2CH3), 2.36 (3H, s, CH3), 1.24 (6H, t, J=5.65 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. washThe product was eluted with hexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-076b73eca32e47f692c987f89ea67dc2
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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