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

HRID 1671492
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HRID 1671492 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 2

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

실험 절차

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).

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후처리

  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)

출처 및 근거

ORD 기록
ord-5e1d25aa90b14e26a8e3de6e59eb7850
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07994318B2

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