Water → 2-(1-Phenylthiocycloprop-1-yl)oxy-5-(trifluoromethoxy)benzenemethanol

HRID 323761

Reaktionsgleichung

Reaktionsgleichung von HRID 323761
[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.[BH4-].[Na+].O>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[CH2:4][OH:5])[CH2:18][CH2:17]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 12680582-Hydroxy-5-(trifluoromethoxy)benzaldehydeHCID 4311764Sodium borohydrideHCID 11000298(1-Iodocyclopropyl)(phenyl)sulfane

Produkt 1

HCID 220069572-(1-Phenylthiocycloprop-1-yl)oxy-5-(trifluoromethoxy)benzenemethanolAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418647HCID 178418647, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Silver carbonate (4.82 g, 17.5 mmol) was added to a solution of 2-hydroxy-5-(trifluoromethoxy)benzaldehyde (2.0 g, 9.7 mmol) and (1-iodocycloprop-1-yl)phenylsulfide (Cohen T. and Matz J. R., J. Am. Chem. Soc. 1980, 102, 6902) (5.48 g, 17.5 mmol) in toluene (25 mL) and the mixture was stirred at 40° C. for 36 h., then at room temperature for 16 h. The mixture was diluted with ethyl acetate and filtered, washing well with ethyl acetate. The mixture was washed with aqueous sodium hydroxide (1M, 6×75 mL) and brine (75 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was dissolved in ethanol, (15 mL), cooled to 0° C. and sodium borohydride, (0.74 g, 19.6 mmol), was added. The mixture was stirred at room temperature for 1 h., poured into water and extracted into ethyl acetate (3×100 mL). The combined organic fractions were dried (MgSO4), and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/EtOAc (97:3 increasing to 70:30), to give the title compound as a yellow oil (1.8 g, 53%). 1H NMR (250 MHz, CDCl3) 1.41-1.44 (2H, m), 1.46-1.51 (2H, m), 1.84 (1H, t, J 6.5 Hz), 4.58 (2H, d, J 6.5 Hz), and 7.18-7.48 (8H, m).

Aufarbeitung

  1. waitat room temperature for 16 h
  2. filtrationfiltered
  3. washwashing well with ethyl acetate
  4. washThe mixture was washed with aqueous sodium hydroxide (1M, 6×75 mL) and brine (75 mL)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated under reduced pressure
  7. dissolutionThe residue was dissolved in ethanol, (15 mL)
  8. temperaturecooled to 0° C.
  9. stirringThe mixture was stirred at room temperature for 1 h.
  10. extractionextracted into ethyl acetate (3×100 mL)
  11. dry with materialThe combined organic fractions were dried (MgSO4)
  12. customthe solvent was evaporated under reduced pressure
  13. customThe residue was purified by flash column chromatography on silica gel
  14. washeluting with hexane/EtOAc (97:3 increasing to 70:30)

Quellen und Nachweise

ORD-Eintrag
ord-e2b46c35ef6a441faab36bc75471cb86
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06214846B1

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