Cesium carbonate → 5-Methoxy-2-(2-mesyloxyethoxy)-benzaldehyde

HRID 1717513

반응식

HRID 1717513 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:18][S:19]([O:22][CH2:23][CH2:24]OS(C)(=O)=O)(=[O:21])=[O:20]>CN(C=O)C>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:2]([O:1][CH2:24][CH2:23][O:22][S:19]([CH3:18])(=[O:21])=[O:20])=[C:3]([CH:6]=1)[CH:4]=[O:5]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 207961,2-Ethanediol, 1,2-dimethanesulfonateHCID 956952-Hydroxy-5-methoxybenzaldehyde

생성물 1

HCID 597658555-Methoxy-2-(2-mesyloxyethoxy)-benzaldehyde수율 78%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
70 °C

실험 절차

To a vigorously stirred solution of 15,2 g (100 mmol) 2-hydroxy-5-methoxy-benzaldehyde and 42.4 g (130 mmol) caesium carbonate in 350 ml DMF at 0° C. was added 27,3 g (125 mmol) 1,2-bis-methanesulfonyloxy-ethane ((J. Med. Chem.; 47; 17; (2004); 4300-4315) in 50 ml DMF dropwisely. The reaction mixture was stirred vigorously at 70° C. for 5 h. The solvent was evaporated. 200 ml water and 200 ml ethyl acetate were added. The organic phase was separated. The aqueous phase was extracted three times with 100 ml ethyl acetate each. The combined organic phases were washed with 50 ml water and 50 ml brine. The organic phase was dried with magnesium sulfate and evaporated. The crude product was purified by silica column chromatography (gradient ethylacetate:hexane 1:6, ethyl acetate→1:2). The desired product 4a was obtained in 78% yield (21.4 g, 78 mmol) as yellow oil.

후처리

  1. customThe solvent was evaporated
  2. addition200 ml water and 200 ml ethyl acetate were added
  3. customThe organic phase was separated
  4. extractionThe aqueous phase was extracted three times with 100 ml ethyl acetate each
  5. washThe combined organic phases were washed with 50 ml water and 50 ml brine
  6. dry with materialThe organic phase was dried with magnesium sulfate
  7. customevaporated
  8. customThe crude product was purified by silica column chromatography (gradient ethylacetate:hexane 1:6, ethyl acetate→1:2)

출처 및 근거

ORD 기록
ord-3d753c14c9994b67aa656b2412c7b636
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803960B2

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