Benzyl Alcohol → Benzyl tetrahydro-2H-pyran-4-carboxylate

HRID 16608

Reaktionsgleichung

Reaktionsgleichung von HRID 16608
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.O=S(Cl)Cl.[CH2:14](O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:8])[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 244Benzyl AlcoholHCID 24386Thionyl ChlorideHCID 219302Oxane-4-carboxylic acid

Produkt 1

HCID 23131611Benzyl tetrahydro-2H-pyran-4-carboxylateAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of tetrahydropyran-4-yl-carboxylic acid (910 mg, 6.99 mmol) and SOCl2 (5.0 mL) was stirred for 1 h at 60° C. and concentrated in vacuo. To the residue were added benzyl alcohol (1.52 g, 14.1 mmol) and tetrahydrofuran (5.0 mL) at ambient temperature. The resulting mixture was stirred for 13 h at ambient temperature and concentrated in vacuo. The residue was purified by preparative thin layer chromatography (silica gel, eluting with hexane/ethyl acetate (2:1)) to give 1.08 g (70%) of the title compound as a pale yellow oil.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. stirringThe resulting mixture was stirred for 13 h at ambient temperature
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative thin layer chromatography (silica gel, eluting with hexane/ethyl acetate (2:1))

Quellen und Nachweise

ORD-Eintrag
ord-8fd06a8b3539453b86ef5bd3c688a452
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737163B2

Verknüpfte Notizen

Wird geladen…