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

HRID 453824

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HRID 453824 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c7d4a2358b2f49a28f5e53ad7b6b46e1
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492549B2

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