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

HRID 1798082Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1798082
[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].[CH2:14]1[CH2:19][O:18][CH:17]=[CH:16][CH2:15]1>ClCCl.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH:17]2[CH2:16][CH2:15][CH2:14][CH2:19][O:18]2)[CH:7]=[C:6]([CH2:11][O:12][CH3:13])[C:3]=1[CH:4]=[O:5]

Komponenten

5

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 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)KatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2,4-dihydroxy-6-methoxymethylbenzaldehyde (4.08 g, 22.4 mmol) in dichloromethane (100 mL) was treated with PPTS (100 mg) and DHP (4.06 mL, 44.8 mmol) at room temperature overnight. The reaction was concentrated to dryness. The residue was purified by the flash column chromatography (silica, hexanes/ethyl acetate=3:1) to afford the title compound (5.18 g, 87%). 1H NMR (300 MHz, CD3OD) δ 12.34 (s, 1H), 10.12 (s, 1H), 6.58 (s, 1H), 6.56 (s, 1H), 5.58 (m, 1H), 4.63 (s, 2H), 3.84-3.81 (m, 1H), 3.66-3.62 (m, 1H), 3.40 (s, 3H), 1.95-1.86 (m, 2H), 1.75-1.62 (m, 4H).

Aufarbeitung

  1. concentrationThe reaction was concentrated to dryness
  2. customThe residue was purified by the flash column chromatography (silica, hexanes/ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-dbf5f27c025d452ca514ccb891a0836f
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343944B2

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