Sodium Carbonate → 4-(Benzo[b]thiophen-5-yl)-3,5-dimethylisoxazole

HRID 1009003ノート

反応式

HRID 1009003 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[CH3:11][C:12]1[C:16](C(B(O)O)=O)=[C:15]([CH3:22])[O:14][N:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(O)C>[S:9]1[CH:8]=[CH:7][C:6]2[CH:10]=[C:2]([C:16]3[C:12]([CH3:11])=[N:13][O:14][C:15]=3[CH3:22])[CH:3]=[CH:4][C:5]1=2

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 27765785-Bromo-1-benzothiopheneHCID 673054143,5-Dimethyl-4-isoxazoylboronic acid

生成物 1

HCID 534868054-(Benzo[b]thiophen-5-yl)-3,5-dimethylisoxazole収率 60.2%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

To a solution of 5-bromo-1-benzothiophene (ABCR, CAS: 133150-64-8, 1.0 6 g, 5.0 mmol) in dimethoxyethane (60 mL) and ethanol (6.0 mL) was added 3,5-dimethyl-4-isoxazoylboronic acid (1.0 g, 7.5 mmol), and 2 m sodium carbonate (2.0 mL). The reaction mixture was degassed 2-3 times, tetrakis-(triphenylphosphine)palladium (0.813 g, 0.7 mmol) was added, and the mixture was stirred for 6 h at 80° C. and concentrated. The residue was taken up in water and extracted with ethyl acetate. The organics were washed, dried and concentrated. The crude product was chromatographed on silica gel using heptane/ethyl acetate as eluent to obtain 4-benzo[b]thiophen-5-yl-3,5-dimethyl-isoxazole (0.69 g) as a light yellow solid. MS (ISP): m/e 230.1 (M+H)+

後処理

  1. additionwas added
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. washThe organics were washed
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product was chromatographed on silica gel

出典と根拠

ORDレコード
ord-38a7e0a2adcd4b80ab7c45ce2197dfc2
出典データセット
uspto-grants-2011_07
特許番号
US07973051B2

反応ノート

読み込み中…