Vanillin → HCID 6484658, compound

HRID 1012209Notes

Reaction equation

HRID 1012209 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[CH3:12][O:13][CH2:14][CH2:15]Br.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O>[CH3:7][O:6][C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][C:8]=1[O:9][CH2:15][CH2:14][O:13][CH3:12])[CH:2]=[O:1]

Participants

6

Reactant 4

HCID 1183VanillinHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl ether

Product 1

HCID 6484658HCID 6484658, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a flask was added vanillin (3.28 g, 21.6 mmol) and 2-bromoethyl methyl ether (3.04 mL, 1.5 equiv) in a solution of DMF (20 mL). K2CO3 (5.5 g, 2 equiv) was then added to the solution and the reaction slurry was stirred at 90° C. for 16 h under N2. The reaction solution was diluted with EtOAc (100 mL), filtered, washed with sat NH4Cl, dried over Na2SO4, filtered and concentrated in vacuo. The crude material was chromatographed (SiO2, Hex/EtOAc 100:D to 70:30) to afford the intermediate compound.

Workup

  1. filtrationfiltered
  2. washwashed with sat NH4Cl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was chromatographed (SiO2, Hex/EtOAc 100:D to 70:30)
  7. customto afford the intermediate compound

Sources & evidence

ORD record
ord-4c340c6134f34f71952ce12dda49b484
Source dataset
uspto-grants-2011_07
Patent number
US07977489B2

Reaction notes

Loading…