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

HRID 1388028Notes

Reaction equation

HRID 1388028 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-ed22a5e725b74087948ea56174faacf0
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

Loading…