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

HRID 1277272ノート

反応式

HRID 1277272 の反応式
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

参加物

7

反応物 3

HCID 962WaterHCID 18472282HCID 18472282、化合物HCID 866453334-Methylphenyl borate

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 1140Toluene溶媒HCID 10340Sodium Carbonate溶媒

実験手順

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.

後処理

  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)]

出典と根拠

ORDレコード
ord-d661db6141a04382a4bf3fb1115be22e
出典データセット
uspto-grants-2000_12
特許番号
US06166006

反応ノート

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