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

HRID 575821노트

반응식

HRID 575821 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-6ba6bf3a8587433f9f890c0626dc4d42
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034900B2

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