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

HRID 566098Notes

Reaction equation

HRID 566098 reaction equation
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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 10340Sodium CarbonateSolvent

Procedure

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.

Workup

  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)]

Sources & evidence

ORD record
ord-c58c87a721444bacbf7bd04d3ebff31d
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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