Ethyl Acetate → (2-Methyl-4-{2-[4-(2-phenoxy-ethoxy)phenyl]-ethyl}-4,5-dihydro-oxazol-4-yl)-methanol

HRID 1865140Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1865140
[OH:1][CH2:2][C:3]1([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH2:7][O:6][C:5]([CH3:8])=[N:4]1.C([O-])([O-])=O.[Cs+].[Cs+].[O:24]([CH2:31][CH2:32]Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CCOC(C)=O>CN(C=O)C.O>[CH3:8][C:5]1[O:6][CH2:7][C:3]([CH2:2][OH:1])([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:32][CH2:31][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:15][CH:16]=2)[N:4]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 68526Benzene, (2-bromoethoxy)-HCID 579352584-[2-(4-Hydroxymethyl-2-methyl-4,5-dihydro-oxazol-4-yl)-ethyl]-phenol

Produkt 1

HCID 66768401(2-Methyl-4-{2-[4-(2-phenoxy-ethoxy)phenyl]-ethyl}-4,5-dihydro-oxazol-4-yl)-methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of 4-[2-(4-hydroxymethyl-2-methyl-4,5-dihydro-oxazol-4-yl)-ethyl]-phenol (300 mg, 1.27 mmol) in DMF (5 ml) was added Cs2CO3 (1.2 g, 3.83 mmol) and 2-phenoxyethyl bromide (770 mg, 1.27 mmol). The reaction mixture was stirred at 85° C. for 4 hours. AcOEt and water were then added, the organic layer was separated and the aqueous phase was extracted with AcOEt (3×50 ml). The combined organic extracts were washed with brine, dried over MgSO4, and evaporated to dryness. Purification by flash chromatography (AcOEt/Hx 9:1) afforded (2-Methyl-4-{2-[4-(2-phenoxy-ethoxy)phenyl]-ethyl}-4,5-dihydro-oxazol-4-yl)-methanol as colorless oil. To a solution of (2-methyl-4-{2-[4-(2-phenoxy-ethoxy)phenyl]-ethyl}-4,5-dihydro-oxazol-4-yl)-methanol (50 mg, 0.14 mmol) in ethanol (2 ml) was added conc. HCl (2 ml). The reaction mixture was stirred at 85° C. for 2 hours, then concentrated to dryness. The residue was re-dissolved in AcOEt and precipitated with hexanes. The solid was filtered off, washed with dry ether and dried in vacuo to afford 2-amino-4-{4-[2-phenoxy-ethoxy]-phenyl}-2-ethoxy-butan-1-ol hydrochloride as a colorless powder. ESI+MS: m/z=332.3 (M+H)+.

Aufarbeitung

  1. customthe organic layer was separated
  2. extractionthe aqueous phase was extracted with AcOEt (3×50 ml)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customPurification by flash chromatography (AcOEt/Hx 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-625ae0b7d0514bbbbff87683a7419f5d
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07625950B2

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