Water → HCID 4526577, compound

HRID 1957940Notes

Reaction equation

HRID 1957940 reaction equation
O[CH:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].C([N:19]([CH2:22][CH3:23])CC)C.[OH2:24].C1C[O:28][CH2:27][CH2:26]1>>[C:11]1([C:2]2[N:19]=[C:22]([C:23]([O:28][CH2:27][CH3:26])=[O:24])[O:4][C:3]=2[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 8400BenzoinHCID 8471Triethylamine

Product 1

HCID 4526577HCID 4526577, compound

Procedure

Ethyl oxalyl chloride (1.1 mL, 10 mmol) will be added dropwise to a stirring solution of 2-hydroxy-1,2-diphenyl ethanone (2.12 g, 10 mmol) and triethyl amine (2.2 mL, 16 mmol) in anhydrous THF (50 mL) under argon. After stirring for 45 min the mixture will be filtered and concentrated, and NH4OAC (4 g, 50 mmol) and acetic acid (50 mL) will be added. The mixture will be heated to reflux for 6 h. The reaction will be brought to room temperature and water will be added and extracted with dichloromethane and the residue will be subjected to column chromatography to yield the title compound.

Workup

  1. filtrationwill be filtered
  2. concentrationconcentrated
  3. additionNH4OAC (4 g, 50 mmol) and acetic acid (50 mL) will be added
  4. temperatureThe mixture will be heated
  5. temperatureto reflux for 6 h
  6. customThe reaction
  7. customwill be brought to room temperature
  8. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-8570e090fa89449587a698fcf37e4817
Source dataset
uspto-grants-2013_04
Patent number
US08410097B2

Reaction notes

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