Water → ethyl 6-(4-methylphenyl)-2H-thiochromene-3-carboxylate

HRID 1388028Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1388028
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[S:8][CH2:7][C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5]2.B([O-])([O-])O[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1.O>C(=O)([O-])[O-].[Na+].[Na+].C(O)C.C1(C)C=CC=CC=1>[CH3:25][C:22]1[CH:23]=[CH:24][C:19]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[S:8][CH2:7][C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5]3)=[CH:20][CH:21]=1

Komponenten

7

Edukt 3

HCID 962WaterHCID 18472282HCID 18472282, VerbindungHCID 866453334-Methylphenyl borate

Produkt 1

HCID 18472236ethyl 6-(4-methylphenyl)-2H-thiochromene-3-carboxylateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Versuchsvorschrift

A solution of ethyl 6-bromo-2H-thiochromene-3-carboxylate (1.00 g, 3.34 mmol), 4-methylphenyl borate (0.55 g, 4.01 mmol) and tetrakistriphenylphosphine palladium (0.19 g, 0.167 mmol) in 2M sodium carbonate (3.5 ml), ethanol (3 ml) and toluene (25 ml) was stirred at 80° C. for 24 hours. To the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with 0.5N hydrochloric acid and saturated brine, and dried with magnesium sulfate. The solvent was evaporated, and the residue was purified with silica gel column chromatography [hexane:ethyl acetate (5:1)] to give ethyl 6-(4-methylphenyl)-2H-thiochromene-3-carboxylate (1.02 g, 99%) as yellow powder.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 0.5N hydrochloric acid and saturated brine
  3. dry with materialdried with magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified with silica gel column chromatography [hexane:ethyl acetate (5:1)]

Quellen und Nachweise

ORD-Eintrag
ord-ed22a5e725b74087948ea56174faacf0
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06268354B1

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