Ethyl Acetate → 7-(methoxymethoxy)-2,2-dimethyl-2H-chromene-3-carbaldehyde

HRID 217427Notes

Reaction equation

HRID 217427 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].[OH:7][C:8]1[CH:15]=[C:14]([O:16][CH2:17][O:18][CH3:19])[CH:13]=[CH:12][C:9]=1[CH:10]=O.[CH3:20][CH:21]([CH3:25])[C:22](=O)C.CCOC(C)=O>O1CCOCC1>[CH3:19][O:18][CH2:17][O:16][C:14]1[CH:15]=[C:8]2[C:9]([CH:10]=[C:20]([CH:1]=[O:4])[C:21]([CH3:25])([CH3:22])[O:7]2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 112513-Methyl-2-butanoneHCID 11430Potassium CarbonateHCID 27550732-Hydroxy-4-(methoxymethoxy)benzaldehyde

Product 1

HCID 584386707-(methoxymethoxy)-2,2-dimethyl-2H-chromene-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

K2CO3 (835 mg) was suspended in dioxane (40 mL), and 2-hydroxy-4-(methoxymethoxy)benzaldehyde (1 g) and 3-methyl 2-butanal (0.787 mL) were added thereto, followed by stirring at 110° C. overnight. EtOAc was added thereto, the insoluble materials were removed by filtration through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=95:5 to 70:30) to obtain 7-(methoxymethoxy)-2,2-dimethyl-2H-chromene-3-carbaldehyde (320 mg) as a yellow oil.

Workup

  1. customthe insoluble materials were removed by filtration through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=95:5 to 70:30)

Sources & evidence

ORD record
ord-99671a6d4e1c40538f60cbc2acc091cd
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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