Potassium Carbonate → HCID 59603127, compound

HRID 2061352Notes

Reaction equation

HRID 2061352 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].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:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5])[CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 956952-Hydroxy-5-methoxybenzaldehyde

Product 1

HCID 59603127HCID 59603127, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension containing 2-hydroxy-5-methoxybenzaldehyde (2.0 g, 13.16 mmol) and K2CO3 (2.18 g, 15.79 mmol) in DMF (20 mL), bromoacetaldehyde diethyl acetal (2.43 mL, 15.79 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 the target compound 23 (1.10 g, 31%) as an oil. 1H NMR (500 MHz, CDCl3): δ: 10.49 (1H, s, CHO), 7.33 (1H, d, J=3.30 Hz, ArH), 7.12 (1H, dd, J=5.75 & 3.30 Hz, ArH), 6.97 (1H, d, J=9.05 Hz), 4.87 (1H, t, J=5.25 Hz, CH), 4.09 (2H, d, J=5.25 Hz, CH2), 3.81-3.78 (2H, m, CH2CH3), 3.67-3.64 (2H, m, CH2CH3), 1.26 (6H, t, J=7.05 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-81b9170605f0405081a91faf49cab259
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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