Chloroform → HCID 58608108, compound

HRID 2243569Notes

Reaction equation

HRID 2243569 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:17][C:11]3[NH:12][CH:13]=[CH:14][C:15](=O)[C:10]=3[C:9]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.C(Cl)(Cl)[Cl:25].C(Cl)(=O)C(Cl)=O>CN(C=O)C>[Cl:25][C:15]1[CH:14]=[CH:13][N:12]=[C:11]2[O:17][C:8]([C:5]3[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=3)=[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:10]=12

Participants

5

Reactant 3

HCID 6212ChloroformHCID 65578Oxalyl chlorideHCID 58608096HCID 58608096, compound

Product 1

HCID 58608108HCID 58608108, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 25-ml round bottom flask equipped with a reflux condenser fitted with a nitrogen inlet adapter was charged with 2-(4-hydroxy-phenyl)-3-phenyl-7H-furo[2,3-b]pyridin-4-one (5) (0.280 g, 0.923 mmol) and chloroform (9.0 mL). Oxalyl chloride (0.469 g, 0.32 mL, 3.69 mmol) and DMF (0.05 mL) were added and the mixture stirred at room temperature until the evolution of gas ceased (approx. 1 min). The mixture was heated at reflux for 5 h. The reaction mixture was concentrated to afford an orange brown solid which was purified via column chromatography on silica gel (eluting with 0-25% ethyl acetate-hexane) to afford 4-(4-chloro-3-phenyl-furo[2,3-b]pyridin-2-yl)-phenol 6 as an orange solid. MS (MH+) 322.0; Calculated 321 for C19H12ClNO2.

Workup

  1. customA 25-ml round bottom flask equipped with a reflux condenser
  2. customfitted with a nitrogen inlet adapter
  3. custom(approx. 1 min)
  4. temperatureThe mixture was heated
  5. temperatureat reflux for 5 h
  6. concentrationThe reaction mixture was concentrated
  7. customto afford an orange brown solid which
  8. customwas purified via column chromatography on silica gel (eluting with 0-25% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-15f5c5857ad04b40b81af22948b91e0d
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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