3,4-dihydro-2H-pyran → 2-Hydroxy-6-methoxymethyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde

HRID 1798060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1798060
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([CH2:11][O:12][CH3:13])[C:3]=1[CH:4]=[O:5].[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1>ClCCl>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][O:14]2)[CH:7]=[C:6]([CH2:11][O:12][CH3:13])[C:3]=1[CH:4]=[O:5]

Komponenten

4

Edukt 2

HCID 80803,4-dihydro-2H-pyranHCID 582926702,4-Dihydroxy-6-methoxymethyl-benzaldehyde

Produkt 1

HCID 582928652-Hydroxy-6-methoxymethyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehydeAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 2,4-dihydroxy-6-methoxymethyl-benzaldehyde (2.62 g, 14.45 mmol) in dichloromethane (50 mL) was added 3,4-dihydro-2H-pyran (2.42 g mL, 28.90 mmol) and pyridium p-toluenesulfonic acid (0.050 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 2-hydroxy-6-methoxymethyl-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde (3.06 g, 80%). 1H NMR (400 MHz, CDCl3) δ 12.30 (s, 1H), 10.10 (s, 1H), 6.80 (s, 1H), 6.79 (s, 1H), 5.47 (s, 1H), 4.60 (s, 2H), 3.80 (m, 1H), 3.60 (m, 1H), 3.40 (s, 3H), 2.00-1.50 (m, 6H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-814f564cd6cf40ac8b409e4e16024295
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343944B2

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