3,4-dihydro-2H-pyran → 2-[(2-Chloro-4-methyl-5-nitrophenyl)methoxy]tetrahydro-2H-pyran

HRID 2173966Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2173966
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12][OH:13].[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12][O:13][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][O:14]1

Komponenten

5

Edukt 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86701534(2-Chloro-4-methyl-5-nitrophenyl)methanol

Produkt 1

HCID 867015352-[(2-Chloro-4-methyl-5-nitrophenyl)methoxy]tetrahydro-2H-pyran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (2-chloro-4-methyl-5-nitrophenyl)methanol (23 g, 114 mmol) and 3,4-dihydro-2H-pyran (20.9 mL, 228 mmol) in CH2Cl2 (500 mL) was added pyridinium p-toluenesulfonate (5.7 g, 22.8 mmol), and then the mixture was stirred at room temperature for 11 h. The reaction was quenched by 5% aq. NaHCO3. The layers were separated and the aqueous layer was extracted with CH2Cl2. The organic layers were combined and washed with H2O and brine, dried over Na2SO4, filtered and concentrated. The resulting residue was purified by SiO2 column chromatography (heptane/EtOAc=96/4, isocratic) to give the title compound. 1H NMR (400 MHz, ACETONITRILE-d3) δ 8.10 (s, 1H), 7.49 (s, 1H), 4.81 (d, J=13.64 Hz, 1H), 4.72-4.78 (m, 1H), 4.59 (d, J=13.64 Hz, 1H), 3.77-3.92 (m, 1H), 3.34-3.60 (m, 1H), 2.54 (s, 3H), 1.68-1.91 (m, 2H), 1.43-1.68 (m, 4H).

Aufarbeitung

  1. customThe reaction was quenched by 5% aq. NaHCO3
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. washwashed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by SiO2 column chromatography (heptane/EtOAc=96/4, isocratic)

Quellen und Nachweise

ORD-Eintrag
ord-86a7e58ae1ab4b3f9bc21e3154d8a303
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056874B2

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