Triethylamine → 3-(3',4',5'-Trimethoxybenzoyl)-7-methoxy-8-hydroxy-2h-chromene

HRID 273199

Reaktionsgleichung

CN(C)[CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=1)=[O:6].[OH:20][C:21]1[C:28]([OH:29])=[C:27]([O:30][CH3:31])[CH:26]=[CH:25][C:22]=1C=O.[CH3:32]CN(CC)CC>[Br-].C([N+]1C(C)=C(CCO)SC=1)C>[CH3:18][O:17][C:9]1[CH:8]=[C:7]([CH:12]=[C:11]([O:13][CH3:14])[C:10]=1[O:15][CH3:16])[C:5]([C:4]1[CH2:31][O:30][C:27]2[C:26]([CH:3]=1)=[CH:25][CH:22]=[C:21]([O:20][CH3:32])[C:28]=2[OH:29])=[O:6]

Komponenten

Reaktionsbedingungen

Temperatur: 115 °C

Versuchsvorschrift

A mixture of 2-(N,N-dimethylamino)ethyl-(3′,4′,5′-trimethoxyphenyl)ketone (4, 1.17 g, 4.37 mmol), 2,3-dihydroxy-4-methoxybenzaldehyde (2, 0.74 g, 4.37 mmol), 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (0.12 g, 0.44 mmol) and Et3N (1 ml) was heated under reflux at 115° C. for 3.5 hours. After quenching with 1M HCl, the product was extracted with CH2Cl2. The combined extract was washed with water, rinsed with brine and dried over anhydrous magnesium sulfate. Purification was done by silica gel flash column chromatography (60:40, hexane-ethyl acetate) which afforded the pure yellow-colored phenol (0.179 g, 0.48 mmol) in 11% yield. The phenol had a melting point of 189-190° C.

Aufarbeitung

temperaturewas heated
customAfter quenching with 1M HCl
extractionthe product was extracted with CH2Cl2
extractionThe combined extract
washwas washed with water
washrinsed with brine
dry with materialdried over anhydrous magnesium sulfate
customPurification

Quellen und Nachweise

ORD-Eintrag: ord-d5ce02cecbb44429899fff1cda686101
Quelldatensatz: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07456214B2

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