alpha-Hydroxyacetophenone → HCID 599077, 화합물

HRID 1581780노트

반응식

HRID 1581780 반응식
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

참가 물질

6

반응물 3

HCID 68490alpha-HydroxyacetophenoneHCID 160693Formamidine acetateHCID 5360545Sodium

생성물 1

HCID 599077HCID 599077, 화합물수율 3,427.5%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 78373Dimethylformamide dimethyl acetal용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c1c64558bac443c3aaec7e07c6c9bec2
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06730792B2

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