alpha-Hydroxyacetophenone → HCID 599077、化合物

HRID 1581780ノート

反応式

HRID 1581780 の反応式
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

参加物

6

反応物 3

HCID 68490alpha-HydroxyacetophenoneHCID 160693Formamidine acetateHCID 5360545Sodium

生成物 1

HCID 599077HCID 599077、化合物収率 3,427.5%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 78373Dimethylformamide dimethyl acetal溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c1c64558bac443c3aaec7e07c6c9bec2
出典データセット
uspto-grants-2004_05
特許番号
US06730792B2

反応ノート

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