Sodium hydride → 1-[4-Benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl]ethanone

HRID 2407257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2407257
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([OH:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CC1C=CC(S(O[CH2:32][C@H:33]2[CH2:35][O:34]2)(=O)=O)=CC=1>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([O:18][CH2:32][C@H:33]2[CH2:35][O:34]2)[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 154187Glycidyl tosylate, (R)-HCID 3092574'-Benzyloxy-2'-hydroxyacetophenone

Produkt 1

HCID 866447131-[4-Benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl]ethanoneAusbeute 63,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 1-(4-(benzyloxy)-2-hydroxyphenyl)ethanone (3.36 g, 13.9 mmol) in anhydrous DMF (15 ml) was added NaH (0.62 g, 15.5 mmol). The mixture was allowed to stir at RT for 30 min, and a solution of (R)-oxiran-2-ylmethyl 4-methylbenzenesulfonate (3.17 g, 13.9 mmol) in DMF was added dropwise at RT. The mixture was slowly heated to 60° C. and stirred for 3 h. The reaction was quenched by addition of water (80 ml) and extracted three times with EtOAc. The combined organic layers were extracted twice with aq 1 M NaOH and washed with water and brine. The organic layer was dried with Na2SO4 and concentrated. The crude product obtained was purified by column chromatography with EtOAc/heptane (1:1) as eluent to afford the title compound (2.64 g) as a white solid.

Aufarbeitung

  1. temperatureThe mixture was slowly heated to 60° C.
  2. stirringstirred for 3 h
  3. customThe reaction was quenched by addition of water (80 ml)
  4. extractionextracted three times with EtOAc
  5. extractionThe combined organic layers were extracted twice with aq 1 M NaOH
  6. washwashed with water and brine
  7. dry with materialThe organic layer was dried with Na2SO4
  8. concentrationconcentrated
  9. customThe crude product obtained
  10. customwas purified by column chromatography with EtOAc/heptane (1:1) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-13283bb344a84b678b0e1c1bddcd8d6d
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809536B2

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