3,4-dihydro-2H-pyran → 6-Chloro-2-hydroxy-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde

HRID 1798052Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1798052
[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([OH:10])[CH:5]=[C:4]([OH:11])[CH:3]=1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1>C(Cl)Cl>[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([OH:10])[CH:5]=[C:4]([O:11][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:12]2)[CH:3]=1

Komponenten

4

Edukt 2

HCID 80803,4-dihydro-2H-pyranHCID 232948482-Chloro-4,6-dihydroxybenzaldehyde

Produkt 1

HCID 866539726-Chloro-2-hydroxy-4-(tetrahydro-pyran-2-yloxy)-benzaldehydeAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 6-chloro-2,4-dihydroxybenzaldehyde (9.0 g, 52.2 mmol) in DCM (150 mL) was added 3,4-dihydro-2H-pyran (9 mL, 98.4 mmol), followed by PPTs (1.31 g, 5.2 mmol). The reaction mixture was stirred at room temperature for 1.5 h and quenched by saturated aqueous NaHCO3 (50 mL) at 0° C. The organic layer was separated, washed with brine (40 mL) and dried over anhydrous Na2SO4. Concentration in vacuo followed by purification with column chromatography on silica gel (EtOAc/PE=1:100) gave the title compound as a colorless oil (10.5 g, Yield: 87.3%). 1H NMR (400 MHz, DMSO-d6) δ12.00 (s, 1H), 10.17 (s, 1H), 6.72-6.78 (m, 1H), 6.57-6.64 (m, 1H), 5.50-5.70 (t, 1H), 3.60-3.73 (m, 2H), 1.55-1.87 (m, 6H) MS (ESI) m/z=257 [M+H]+.

Aufarbeitung

  1. customquenched by saturated aqueous NaHCO3 (50 mL) at 0° C
  2. customThe organic layer was separated
  3. washwashed with brine (40 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationConcentration in vacuo
  6. customfollowed by purification with column chromatography on silica gel (EtOAc/PE=1:100)

Quellen und Nachweise

ORD-Eintrag
ord-b798f3974ad94b8fae994283a4c10173
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343944B2

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