Triethylamine → 7-(Hydroxymethyl)-4-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one
Reaktionsgleichung
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[C:16]3[C:11](=[CH:12][C:13]([C:17](O)=[O:18])=[CH:14][CH:15]=3)[O:10][C:9](=[O:20])[CH:8]=2)[N:6]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[BH4-].[Na+]>C1COCC1.O>[OH:18][CH2:17][C:13]1[CH:12]=[C:11]2[C:16]([C:7]([C:5]3[N:6]=[C:2]([CH3:1])[S:3][CH:4]=3)=[CH:8][C:9](=[O:20])[O:10]2)=[CH:15][CH:14]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of 4-(2-methyl-1,3-thiazol-4-yl)-2-oxo-2H-chromene-7-carboxylic acid (0.692 g, 2.41 mmol) in THF (16 ml) at 0° C. was added triethylamine (1.3 ml, 9.63 mmol) followed by isobutyl chloroformate (0.94 ml, 7.23 mmol) over 15 min. The reaction mixture was stirred at 0° C. for 1 h and sodium borohydride (0.456 g, 12.0 mmol) in water (12 ml) was added. The reaction mixture was stirred 1 h at 0° C., quenched with a solution of NH4Cl and extracted with EtOAc. The organic phase was washed with brine, dried over MgSO4 and evaporated to dryness. The residue was purified by chromatography on silica gel (hexanes-EtOAc, 4:6 to 2:8) to give the title compound. 1H NMR (400 MHz, acetone-d6): δ 8.22 (m, 1H), 8.05 (s, 1H), 7.40 (s, 1H), 7.35 (m, 1H), 6.62 (s, 1H), 4.80 (m, 2H), 4.55 (m, 1H), 2.82 (s, 3H).
Aufarbeitung
- stirringThe reaction mixture was stirred 1 h at 0° C.
- customquenched with a solution of NH4Cl
- extractionextracted with EtOAc
- washThe organic phase was washed with brine
- dry with materialdried over MgSO4
- customevaporated to dryness
- customThe residue was purified by chromatography on silica gel (hexanes-EtOAc, 4:6 to 2:8)
Quellen und Nachweise
- ORD-Eintrag
- ord-a1a21449777340f4977136730014519f
- Quelldatensatz
- uspto-grants-2009_06
- Patentnummer
- US07553973B2
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