Potassium Phosphate, Tribasic → Methyl 5-methoxy-3-methylbenzo[b]thiophene-2-carboxylate

HRID 2283682ノート

反応式

HRID 2283682 の反応式
CB(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:13]1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.Cl[C:48]1[C:52]2[CH:53]=[C:54]([O:57][CH3:58])[CH:55]=[CH:56][C:51]=2[S:50][C:49]=1[C:59]([O:61][CH3:62])=[O:60]>O1CCOCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:58][O:57][C:54]1[CH:55]=[CH:56][C:51]2[S:50][C:49]([C:59]([O:61][CH3:62])=[O:60])=[C:48]([CH3:13])[C:52]=2[CH:53]=1

参加物

9

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 139377Methylboronic AcidHCID 2801561Methyl 3-chloro-5-methoxy-1-benzothiophene-2-carboxylateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl

生成物 1

HCID 12561472Methyl 5-methoxy-3-methylbenzo[b]thiophene-2-carboxylate

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

Methyl boronic acid (120 mg), potassium phosphate (849 mg), water (0.30 ml), palladium acetate (22 mg), and 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl biphenyl (95 mg) were added to a solution of methyl 3-chloro-5-methoxy-1-benzothiophene-2-carboxylate (257 mg) in 1,4-dioxane (3.0 ml), and the reaction solution was stirred at 100° C. for 12 hours. The reaction solution was diluted with ethyl acetate and washed successively with an aqueous ammonium chloride solution, an aqueous sodium bicarbonate solution, and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The resultant residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate) to obtain methyl 5-methoxy-3-methylbenzo[b]thiophene-2-carboxylate.

後処理

  1. washwashed successively with an aqueous ammonium chloride solution
  2. dry with materialAfter drying over anhydrous sodium sulfate
  3. customthe solvent was evaporated under vacuum
  4. customThe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-ade2f2939fc04385b686a0b1e7d7f253
出典データセット
uspto-grants-2015_09
特許番号
US09145414B2

反応ノート

読み込み中…