Trifluoroacetic acid → 6-Phenethyl-dihydro-pyran-2,4-dione

HRID 1839865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1839865
C([O:5][C:6](=[O:21])[CH2:7][C:8](=[O:20])[CH2:9][CH:10](O)[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:11]([CH:10]1[O:21][C:6](=[O:5])[CH2:7][C:8](=[O:20])[CH2:9]1)[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 695267015-Hydroxy-3-oxo-7-phenyl-heptanoic acid tert-butyl ester

Produkt 1

HCID 695272756-Phenethyl-dihydro-pyran-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 5-hydroxy-3-oxo-7-phenyl-heptanoic acid tert-butyl ester (0.96 g, 3.3 mmol) and TFA (0.38 g, 3.3 mmol) in DCM (60 mL) was stirred at rt for 18 h. Removal of the volatile components under reduced pressure afforded the product 6-Phenethyl-dihydro-pyran-2,4-dione as an off white solid (0.56 g, 78%). 1H NMR (300 MHz, CDCl3) δ1.9-2.2 (m, 2H), 2.4-2.7 (m, 2H), 2.75-2.95 (m, 2 H), 3.5 (q, 2H), 4.55-4.65(m, 1H), 7.10-7.35 (m, 5H). ESMS calcd (C13H14O3): 218.1; found: 219.1 (M+H)+.

Aufarbeitung

  1. customRemoval of the volatile components under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-192edaad9d7846aea597bdbd1b83dc65
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06677462B2

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