Trifluoroacetic acid → 7-hydroxy-4-methyl-2H-chromene-3-carbaldehyde

HRID 217459

Reaction equation

HRID 217459 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([CH3:21])=[C:14]([CH:19]=[O:20])[CH2:15][O:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.CC1C=C(C)C(C)=C(C)C=1C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([CH3:21])=[C:14]([CH:19]=[O:20])[CH2:15][O:16]2)=[CH:11][CH:10]=1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12784PentamethylbenzeneHCID 516892Sodium BicarbonateHCID 58438777HCID 58438777, compound

Product 1

HCID 584391347-hydroxy-4-methyl-2H-chromene-3-carbaldehydeYield 83.3%

Procedure

To 7-(benzyloxy)-4-methyl-2H-chromene-3-carbaldehyde (230 mg) and 1,2,3,4,5-pentamethylbenzene (608 mg) was added TFA (3 mL), followed by stirring at room temperature overnight. The reaction liquid was poured into an aqueous NaHCO3 solution, followed by extraction with EtOAc three times. The organic layer was combined, washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=80:20 to 20:80) to obtain 7-hydroxy-4-methyl-2H-chromene-3-carbaldehyde (130 mg) as a pale yellow powder.

Workup

  1. customThe reaction liquid
  2. extractionfollowed by extraction with EtOAc three times
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=80:20 to 20:80)

Sources & evidence

ORD record
ord-4ebbd41767474eba8cde355d40fd4ffc
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Linked notes

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