3,4-dihydro-2H-pyran → methyl 4-(2-hydroxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl)-4-oxobutanoate

HRID 1798038Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1798038
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][C:6]([C:8]1[C:13](C)=[CH:12][C:11]([OH:15])=[CH:10][C:9]=1[OH:16])=[O:7].[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1>ClCCl>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([O:15][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][O:18]2)=[CH:10][C:9]=1[OH:16])=[O:7]

Komponenten

4

Edukt 2

HCID 80803,4-dihydro-2H-pyranHCID 582926554-(2,4-Dihydroxy-6-methyl-phenyl)-4-oxo-butyric acid methyl ester

Produkt 1

HCID 59525512methyl 4-(2-hydroxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl)-4-oxobutanoateAusbeute 84,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 4-(2,4-dihydroxy-6-methyl-phenyl)-4-oxo-butyric acid methyl ester (1.0 g, 4.20 mmol) in dichloromethane (50 mL) was added 3,4-dihydro-2H-pyran (0.38 mL, 8.40 mmol) and pyridium p-toluenesulfonic acid (0.010 g) at room temperature. The resulting mixture was stirred at room temperature for 16 hours then concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give 4-[2-hydroxy-4-(tetrahydro-pyran-2-yloxy)-phenyl]-4-oxo-butyric acid methyl ester (1.1 g, 81%). 1HNMR (400 MHz, CDCl3): 12.40 (s, 1H), 6.95 (s, 1H), 6.90 (s, 1H), 5.90 (br s, 1H), 3.27 (t, J=7.8 Hz, 2H), 2.78 (t, J=7.8 Hz, 2H), 2.30 (s, 3H).

Aufarbeitung

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by silica gel flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cf19c206a4094127922e92424e827f57
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343944B2

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