Cesium fluoride → HCID 11105918, 화합물

HRID 2043319노트

반응식

HRID 2043319 반응식
Br[CH:2]=[C:3]1[O:7][C:6](=[O:8])[CH:5]=[CH:4]1.[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1B(O)O.[F-].[Cs+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O.[Cl-].[Na+].O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1/[CH:2]=[C:3]1/[CH:4]=[CH:5][C:6](=[O:8])[O:7]/1

참가 물질

9

반응물 3

HCID 25953Cesium fluorideHCID 27339602-Thiopheneboronic acidHCID 672283605-(Bromomethylidene)furan-2(5H)-one

생성물 1

HCID 11105918HCID 11105918, 화합물

시약·촉매·용매 5

HCID 67553Tetrabutylammonium Iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 1140Toluene용매HCID 57417360Sodium chloride; water용매

실험 절차

A mixture containing 5-bromomethylene-2(5H)furanone (0.175 g, 1 mmol), 2-thiopheneboronic acid (0.154 g, 1.2 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (0.035 g, 0.05 mmol), tetrabutylammonium iodide (0.018 g, 0.05 mmol) and cesium fluoride (0.456 g, 3 mmol) in toluene (10 mL) and water (10 mL) were stirred at reflux for 24 hours under nitrogen. After cooling, brine (50 mL) was added and the product extracted with ethyl acetate (50 mL×3). The organic fractions were combined, washed with brine (50 mL×3), dried over anhydrous sodium sulfate and evaporated to dryness to give a brown solid. The resulting solid was chromatographed (silica gel: eluent 50:50 dichloromethane/light petroleum) giving the desired product 32 as a yellow powder. Yield 0.170 g (95%), m.p. 100-102° C. 1H NMR (CDCl3) δ 7.50 (d, J=4.9 Hz, 1H, H3′), 7.46 (d, J=5.3 Hz, 1H, H4), 7.38 (d, J=3.4 Hz, 1H, H5′), 7.08-7.05 (m, 1H, H4′), 6.31 (s, 1H, H6), 6.17 (d, J=5.3 Hz, 1H, H3). 13C NMR (CDCl3, 75 MHz) δ 169.5 (C), 146.6 (C), 143.8 (CH), 136.0 (C), 131.3 (CH), 130.7 (CH), 127.7 (CH), 118.0 (CH), 107.5 (CH). IR (Nujol) 1777, 1738, 1459, 1417, 1376, 1107, 935, 886, 731 cm−1.

후처리

  1. temperatureat reflux for 24 hours under nitrogen
  2. temperatureAfter cooling
  3. extractionthe product extracted with ethyl acetate (50 mL×3)
  4. washwashed with brine (50 mL×3)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness
  7. customto give a brown solid
  8. customThe resulting solid was chromatographed (silica gel: eluent 50:50 dichloromethane/light petroleum)

출처 및 근거

ORD 기록
ord-5eacf4f945744735a5011a4c9882a875
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586618B2

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