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

HRID 583029

反応式

HRID 583029 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418647HCID 178418647、化合物触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
40 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-1ce75249449b4a68a0bfbbefc1cd40c5
出典データセット
uspto-grants-1999_07
特許番号
US05929054

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