2-Hydroxy-5-(trifluoromethoxy)benzaldehyde → 2-(1-Phenylthiocycloprop-1-yl)oxy-5-(trifluoromethoxy)benzaldehyde

HRID 583029

반응식

HRID 583029 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][C:3]=1[CH:4]=[O:5].I[C:16]1([S:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:18][CH2:17]1>C1(C)C=CC=CC=1.C(OCC)(=O)C.C(=O)([O-])[O-].[Ag+2]>[C:20]1([S:19][C:16]2([O:1][C:2]3[CH:9]=[CH:8][C:7]([O:10][C:11]([F:12])([F:13])[F:14])=[CH:6][C:3]=3[CH:4]=[O:5])[CH2:18][CH2:17]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

6

반응물 2

HCID 12680582-Hydroxy-5-(trifluoromethoxy)benzaldehydeHCID 11000298(1-Iodocyclopropyl)(phenyl)sulfane

생성물 1

HCID 215840782-(1-Phenylthiocycloprop-1-yl)oxy-5-(trifluoromethoxy)benzaldehyde수율 27%

시약·촉매·용매 3

HCID 178418647HCID 178418647, 화합물촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
40 °C

실험 절차

Silver carbonate (1.2 g, 4.34 mmol) was added to a solution of 2-hydroxy-5-(trifluoromethoxy)benzaldehyde (0.5 g, 2.43 mmol) and (1-iodocycloprop-1-yl)phenylsulfide (Cohen T. and Matz J. R., J. Am. Chem. Soc. 1980, 102, 6902) (1.2 g, 4.34 mmol) in toluene (30 mL) and the mixture was stirred at 40° C. overnight. The mixture was cooled, diluted with ethyl acetate and filtered, washing well with ethyl acetate. The mixture was washed with aqueous sodium hydroxide, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/Et2O (95:5), to give the title compound as a yellow oil (191 mg, 27%). 1H NMR (360 MHz, CDCl3) δ1.51-1.56 (2 H, m), 1.44-1.48 (2 H, m), 7.25-7.35 (7 H, m), 7.69 (1 H, d, J 2.0 Hz), and 10.26 (1 H, s).

후처리

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washwashing well with ethyl acetate
  4. washThe mixture was washed with aqueous sodium hydroxide
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel
  8. washeluting with hexane/Et2O (95:5)

출처 및 근거

ORD 기록
ord-1ce75249449b4a68a0bfbbefc1cd40c5
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05929054

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