Hydrochloric Acid → ethyl 8-formyl-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 855053

Reaktionsgleichung

[OH:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([CH3:10])=[CH:4][C:3]=1[CH:11]=O.C([O-])([O-])=O.[K+].[K+].[F:19][C:20]([F:29])([F:28])/[CH:21]=[CH:22]/[C:23]([O:25][CH2:26][CH3:27])=[O:24].Cl>CN(C=O)C>[CH:8]([C:7]1[CH:6]=[C:5]([CH3:10])[CH:4]=[C:3]2[C:2]=1[O:1][CH:21]([C:20]([F:19])([F:29])[F:28])[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:11]2)=[O:9]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 2-hydroxy-5-methyl-1,3-benzenedicarboxaldehyde (5.0 g, 30.46 mmole), K2CO3 (8.41 g, 60.92 mmole) and ethyl 4,4,4-trifluorocrotonate (7.68 g, 45.69 mmole) in anhydrous DMF (40.0 mL) was heated to 80° C. under a dry N2 atmosphere for 18 hrs. The mixture was then cooled, poured into 1.2 N HCl (100 mL) and extracted with EtOAc (2×100 mL). The combined extracts were washed with brine (100 mL), dried over MgSO4, filtered and concentrated in vacuo to give a dark red oil which was subject to flash chromatography (silica gel) and eluted with 50% CH2Cl2/hexane to give a light yellow solid (2.2 g, 23%): GCMS m/z 314.0 (M+). 1H NMR (CDCl3/400 MHz) 10.42 (s, 1H), 7.70 (s, 1H), 7.65 (s, 1H), 7.26 (s, 1H), 5.80 (q, 1H, J=7.0 Hz), 4.33 (m, 2H), 2.32 (s, 3H), 1.35 (m, 3H).

Aufarbeitung

temperatureThe mixture was then cooled
extractionextracted with EtOAc (2×100 mL)
washThe combined extracts were washed with brine (100 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give a dark red oil which
washeluted with 50% CH2Cl2/hexane

Quellen und Nachweise

ORD-Eintrag: ord-bb945c3a67784ff7a0e5e5f5bc3fc884
Quelldatensatz: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07259266B2

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