m-Chloroperbenzoic acid → Acetic acid 5-benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl ester

HRID 2407264Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2407264
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH2:19][C@H:20]2[CH2:22][O:21]2)=[C:13](C(=O)C)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=[C:26]([C:30]([O:32]O)=[O:31])C=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH2:19][C@H:20]2[CH2:22][O:21]2)=[C:13]([O:32][C:30](=[O:31])[CH3:26])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 86644716HCID 86644716, Verbindung

Produkt 1

HCID 86644717Acetic acid 5-benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl esterAusbeute 52,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-[5-benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl]ethanone (1.0 g, 3.36 mmol) in DCM (20 ml) was added m-chloroperbenzoic acid (1.24 g) and solid NaHCO3 (3.24 g). The mixture was stirred at RT for 3 d. The mixture was filtered and the filtrate washed once with 10% NaHSO4 solution and then twice with NaHCO3 solution. The organic layer was washed with water and brine and dried with Na2SO4. The solvent was removed under reduced pressure. The residue was triturated with ether to give the title compound (0.55 g) as a white solid, which was used without purification.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. washthe filtrate washed once with 10% NaHSO4 solution
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried with Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-6440fab3bd1c423c95a8fd5797d8c7ca
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809536B2

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