Hexamethylenetetramine → 2-oxo-2H-chromene-6-carbaldehyde

HRID 1795443Notes

Reaction equation

HRID 1795443 reaction equation
[O:1]=[C:2]1[C:7](CC2C=CC=CC=2)=[C:6](C)[C:5]2[CH:16]=[CH:17][C:18](O)=[CH:19][C:4]=2[O:3]1.C1N2CN3CN(C2)CN1C3.[C:31](O)(C(F)(F)F)=[O:32]>>[CH:31]([C:19]1[CH:18]=[CH:17][CH:16]=[C:5]2[C:4]=1[O:3][C:2](=[O:1])[CH:7]=[CH:6]2)=[O:32].[CH:31]([C:17]1[CH:16]=[C:5]2[C:4](=[CH:19][CH:18]=1)[O:3][C:2](=[O:1])[CH:7]=[CH:6]2)=[O:32]

Participants

5

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 53385383-Benzyl-4-methylumbelliferone

Product 2

HCID 27358312-oxo-2H-chromene-6-carbaldehydeHCID 222183932-oxo-2H-chromene-8-carbaldehyde

Procedure

2-Oxo-3-benzyl-4-methyl-7-hydroxyl-2H-1-benzopyrane (512 mg, Example 1) and HMTA (140 mg) are mixed in TFA (5 mL). The reaction mixture is heated at reflux overnight. The solvent is removed under reduced pressure. The residue is purified over silica gel column (Hexanes:EtOAc, 85:15) to afford the desired 8-formyl coumarin (107 mg) and 6-formyl coumarin derivative (35 mg).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux overnight
  3. customThe solvent is removed under reduced pressure
  4. customThe residue is purified over silica gel column (Hexanes:EtOAc, 85:15)

Sources & evidence

ORD record
ord-d2dea59c601545ffa822fb0ffecf1a52
Source dataset
uspto-grants-2006_04
Patent number
US07026491B2

Reaction notes

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