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

HRID 1277272노트

반응식

HRID 1277272 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 702Ethanol용매HCID 1140Toluene용매HCID 10340Sodium Carbonate용매

실험 절차

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.

후처리

  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)]

출처 및 근거

ORD 기록
ord-d661db6141a04382a4bf3fb1115be22e
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06166006

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