Cesium carbonate → 4-(4-Bromo-3,5-dimethylphenoxy)tetrahydro-2H-pyran

HRID 237451Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 237451
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].C([O-])([O-])=O.[Cs+].[Cs+].CS(O[CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)(=O)=O>CN1CCCC1=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:4][C:3]=1[CH3:10]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 819704-Bromo-3,5-dimethylphenolHCID 11344352Oxan-4-yl methanesulfonate

Produkt 1

HCID 866971154-(4-Bromo-3,5-dimethylphenoxy)tetrahydro-2H-pyran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution of 4-bromo-3,5-dimethylphenol (3 g) in N-methyl-pyrrolidone (10 mL) is slowly added Cs2CO3 (9.7 g) and tetrahydro-2H-pyran-4-yl methanesulfonate (5.4 g). The mixture is heated for 3 hours at 140° C. After cooling to room temperature the mixture is partitioned between saturated aqueous Na2CO3 solution and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined organic phases are dried (MgSO4). The solvents are evaporated and the residue is purified by HPLC on reversed phase to give the title compound. Yield: 1.2 g; LC (method 4): tR=1.83 min.

Aufarbeitung

  1. temperatureAfter cooling to room temperature the mixture
  2. customis partitioned between saturated aqueous Na2CO3 solution and ethyl acetate
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. dry with materialthe combined organic phases are dried (MgSO4)
  5. customThe solvents are evaporated
  6. customthe residue is purified by HPLC on reversed phase

Quellen und Nachweise

ORD-Eintrag
ord-681e0752718944dfa4ac8743b00107c0
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642585B2

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