Water → HCID 68565476, Verbindung

HRID 1593544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1593544
[OH:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]([CH3:14])([CH2:12][CH3:13])[C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:24][CH2:25][CH2:26][O:27]CC1C=CC=CC=1.O>CN(C=O)C.CO.[Pd]>[OH:27][CH2:26][CH2:25][CH2:24][O:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]([CH3:14])([CH2:12][CH3:13])[C:8]([O:10][CH3:11])=[O:9])=[CH:15][CH:16]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 2776064Benzyl 3-Bromopropyl EtherHCID 21111741Methyl 2-(4-hydroxyphenoxy)-2-methylbutanoate

Produkt 1

HCID 68565476HCID 68565476, VerbindungAusbeute 98,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To a solution of methyl 2-(4-hydroxyphenoxy)-2-methylbutanoate (5 g, 22.32 mmol) in 30 mL DMF was added cesium carbonate (8.7 g, 26.7 mmol) followed by benzyl 3-bromopropyl ether (7.7 g, 33.6 mmol). The solution was stirred at 45° C. for 24 hr, cooled and poured over water. Extraction with AcOEt followed by washing the extracts with water, drying over anhydrous Na2SO4 and concentrating under reduced pressure gave the crude residue. Purification over silica gel using AcOEt/hexanes furnished the desired alkylated derivative (8.25 g). This product was taken up in MeOH (75 mL) and hydrogenated over 10% Pd/C at 40 psi to provide methyl 2-(4-(3-hydroxypropoxy)phenoxy)-2-methylbutanoate (6.23 g, quantitative).

Aufarbeitung

  1. temperaturecooled
  2. extractionExtraction with AcOEt
  3. washby washing the extracts with water
  4. dry with materialdrying over anhydrous Na2SO4
  5. concentrationconcentrating under reduced pressure
  6. customgave the crude residue
  7. customPurification over silica gel
  8. customfurnished the desired alkylated derivative (8.25 g)

Quellen und Nachweise

ORD-Eintrag
ord-a39f231c7467404392cb916e37e21d85
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07297715B2

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