Dimethylformamide → 5-Fluoro-2-((R)-1-(oxiranylmethoxy)-phenyl]-ethanone

HRID 2366032

反応式

HRID 2366032 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5](O)=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.CC1C=CC(S([O:22][CH2:23][C@@H:24]2[O:26][CH2:25]2)(=O)=O)=CC=1.C(=O)([O-])[O-:28].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.O>[F:1][C:2]1[CH:3]=[CH:4][CH2:5][C@:6]([CH2:8][CH:9]=[O:28])([O:22][CH2:23][CH:24]2[CH2:25][O:26]2)[CH:7]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 959922-Acetyl-4-fluorophenolHCID 154187Glycidyl tosylate, (R)-

生成物 1

HCID 866447235-Fluoro-2-((R)-1-(oxiranylmethoxy)-phenyl]-ethanone収率 76%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

A mixture of 5′-fluoro-2′-hydroxyacetophenone (2.04 g, 13.25 mmol), (2R)-(−)-glycidyl tosylate (2.75 g, 12.05 mmol), potassium carbonate (2.16 g, 15.66 mmol) and N,N-dimethyl formamide (20 ml) was heated to 60° C. After 6 hours the reaction mixture was cooled down, water (20 ml) and ethyl acetate (20 ml) were added and the layers were separated. Organic phase was recovered and water layer was extracted twice with ethyl acetate. Organic phase and ethyl acetate extracts were combined and washed twice with water and evaporated to dryness. The crude product was crystallized from 2-propanol to yield 1.91 g (76%) of the pure title compound.

後処理

  1. temperatureAfter 6 hours the reaction mixture was cooled down
  2. customthe layers were separated
  3. customOrganic phase was recovered
  4. extractionwater layer was extracted twice with ethyl acetate
  5. washwashed twice with water
  6. customevaporated to dryness
  7. customThe crude product was crystallized from 2-propanol

出典と根拠

ORDレコード
ord-1b205b8dac5d4d28a11c225a39f567c9
出典データセット
uspto-grants-2014_04
特許番号
US08697723B2

関連ノート

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