Potassium Carbonate → 2-Methyl-5-methylsulfonyl-2,3-dihydro-1-benzofuran

HRID 575821

反応式

HRID 575821 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([CH3:10])[CH2:7][C:6]=2[CH:11]=1.[CH3:12][S:13]([O:15][Na])=[O:14].N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[CH3:10][CH:8]1[CH2:7][C:6]2[CH:11]=[C:2]([S:13]([CH3:12])(=[O:15])=[O:14])[CH:3]=[CH:4][C:5]=2[O:9]1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 133016015-Bromo-2-methyl-2,3-dihydro-1-benzofuranHCID 178504973HCID 178504973、化合物

生成物 1

HCID 1180220192-Methyl-5-methylsulfonyl-2,3-dihydro-1-benzofuran収率 50%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒

実験手順

A mixture of 5-bromo-2-methyl-2,3-dihydro-1-benzofuran (1.0 g, 4.72 mmol), CH3SO2Na (730 mg, 7.08 mmol), L-proline (110 mg, 0.94 mmol), K2CO3 (120 mg, 0.94 mmol) and CuI (89 mg, 0.47 mmol) in DMSO (10 mL) was irradiated at 140° C. for 2 h under microwave. The mixture was extracted with EtOAc (2×30 mL). The combined organic layers were washed with brine (30 mL), dried over Na2SO4, filtered and concentrated to give the crude product that was purified by column chromatography on silica gel (PE/EA=2/1) to give the title compound (500 mg, 50%). 1H NMR (CDCl3, 400 MHz) δ 7.71-7.70 (m, 2H), 6.86-6.82 (m, 1H), 5.08-5.03 (m, 1H), 3.41-3.35 (m, 1H), 3.02 (s, 3H), 2.89-2.83 (m, 1H), 1.56 (d, J=6.4 Hz, 3H).

後処理

  1. customwas irradiated at 140° C. for 2 h under microwave
  2. extractionThe mixture was extracted with EtOAc (2×30 mL)
  3. washThe combined organic layers were washed with brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product that
  8. customwas purified by column chromatography on silica gel (PE/EA=2/1)

出典と根拠

ORDレコード
ord-6ba6bf3a8587433f9f890c0626dc4d42
出典データセット
uspto-grants-2015_05
特許番号
US09034900B2

関連ノート

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