Water → 4-Methoxy-3-(2,2,2-trifluoroethoxy)benzaldehyde

HRID 1098523노트

반응식

HRID 1098523 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].I[CH2:13][C:14]([F:17])([F:16])[F:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[O:1][CH2:13][C:14]([F:17])([F:16])[F:15]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12127IsovanillinHCID 677091,1,1-Trifluoro-2-iodoethane

생성물 1

HCID 126475004-Methoxy-3-(2,2,2-trifluoroethoxy)benzaldehyde

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

3-Hydroxy-4-methoxy-benzaldehyde (560, 2.9 g, 19.5 mmol), 2-iodo-1,1,1-trifluoroethane (561, 2.2 mL, 23 mmol), and potassium carbonate (3.7 g, 27 mmol) were dissolved in N,N-dimethylformamide (100 mL). The solution was stirred at 90° C. overnight under an atmosphere of nitrogen. The reaction was poured into water, extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The compound was isolated by silica gel column chromatography eluting with 25% to 50% ethyl acetate in hexanes to give white powder (562, 1.6 g, 40%).

후처리

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe compound was isolated by silica gel column chromatography
  7. washeluting with 25% to 50% ethyl acetate in hexanes
  8. customto give white powder (562, 1.6 g, 40%)

출처 및 근거

ORD 기록
ord-16ac0bb2a9084cb580e4d1c9bf49322d
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143271B2

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