alpha-Hydroxyacetophenone → HCID 599077, compound

HRID 1581780Notes

Reaction equation

HRID 1581780 reaction equation
O[CH2:2][C:3]([C:5]1C=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[C:11]([OH:14])(=O)[CH3:12].[CH:15]([NH2:17])=[NH:16].[Na]>COC(OC)N(C)C.C(O)C>[N:16]1[CH:2]=[CH:3][C:5]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:12][C:11]=2[OH:14])=[N:17][CH:15]=1

Participants

6

Reactant 3

HCID 68490alpha-HydroxyacetophenoneHCID 160693Formamidine acetateHCID 5360545Sodium

Product 1

HCID 599077HCID 599077, compoundYield 3,427.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

2-Hydroxyacetophenone (220 mmol, 30 g) is stirred in a mixture of dimethylformamide-dimethyl acetal for 5 hours at 70° C., cooled and recrystallised from diethylether. The intermediate is dissolved in dry ethanol (200 ml) and formamidine acetate (0.61 mmol, 63.5 g) is added. A solution of sodium (0.61 mol, 14 g) in ethanol (450 ml) is added in several portions and the mixture is refluxed for 18 hours and evaporated. Recrystallisation from diisopropylether yielded 3.6 g (10%) of 2-(pyrimidin-4-yl)phenol as a solid. This phenolic product is reacted with (2S)-glycidyl 3-nitrobenzenesulfonate substantially as described for Epoxide 1 to yield the title epoxide.

Workup

  1. temperaturecooled
  2. customrecrystallised from diethylether
  3. dissolutionThe intermediate is dissolved in dry ethanol (200 ml)
  4. temperaturethe mixture is refluxed for 18 hours
  5. customevaporated
  6. customRecrystallisation from diisopropylether

Sources & evidence

ORD record
ord-c1c64558bac443c3aaec7e07c6c9bec2
Source dataset
uspto-grants-2004_05
Patent number
US06730792B2

Reaction notes

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