3,4-dihydro-2H-pyran → benzyl 3-(tetrahydro-2H-pyran-2-yloxy)propanoate

HRID 1517861

Reaktionsgleichung

Reaktionsgleichung von HRID 1517861
[OH:1][CH2:2][CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[CH2:14]1[CH2:19][O:18][CH:17]=[CH:16][CH2:15]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>ClCCl>[O:18]1[CH2:19][CH2:14][CH2:15][CH2:16][CH:17]1[O:1][CH2:2][CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

Komponenten

5

Edukt 3

HCID 80803,4-dihydro-2H-pyranHCID 84459Propanoic acid, 3-hydroxy-, phenylmethyl esterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Produkt 1

HCID 66669830benzyl 3-(tetrahydro-2H-pyran-2-yloxy)propanoateAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a mixture of benzyl 3-hydroxypropanoate (2.041 g, 11.34 mmol) and DHP (1.428 g, 17.01 mmol, Alfa) in 30 mL of dichloromethane was added PPTS (0.283 g, 1.13 mmol, Aldrich) slowly. After stirring at 40° C. for 3 days, the reaction mixture was concentrated in vacuo, and the residue was purified by a silica gel column chromatography (PE: EtOAc=20:1) to afford the title compound as pale yellow oil (2.64 g, 88.3%).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by a silica gel column chromatography (PE: EtOAc=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-3a49f357bda14a7aa160ce7ffa5caf9d
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232294B2

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