(4-Methoxyphenyl)boronic acid → 4-(4-methoxyphenyl)-5,5-dimethylfuran-2(5H)-one

HRID 537910

반응식

HRID 537910 반응식
FC(F)(F)S(O[C:7]1[C:8]([CH3:14])([CH3:13])[O:9][C:10](=[O:12])[CH:11]=1)(=O)=O.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.[F-].[K+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.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.C1(C)C=CC=CC=1.O>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:7]2[C:8]([CH3:14])([CH3:13])[O:9][C:10](=[O:12])[CH:11]=2)=[CH:21][CH:20]=1

참가 물질

7

반응물 3

HCID 201262(4-Methoxyphenyl)boronic acidHCID 522689Potassium FluorideHCID 589263482,2-Dimethyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate

생성물 1

HCID 589262544-(4-methoxyphenyl)-5,5-dimethylfuran-2(5H)-one

시약·촉매·용매 3

HCID 66133Benzyl triethylammonium chloride촉매HCID 178418476HCID 178418476, 화합물촉매HCID 22272177Toluene water용매

반응 조건

온도
50 °C

실험 절차

To a 1:1 mixture of toluene/water (20 mL), were added 2,2-dimethyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate (100 mg, 0.38 mmol), 4-methoxyphenylboronic acid (87 mg, 0.57 mmol), PdCl2(PPh3)2 (27 mg, 0.038 mmol), 2M KF aqueous solution (0.95 mL, 1.9 mmol), benzyltriethylammonium chloride (8.7 mg, 0.038 mmol). The mixture was heated at 50° C. under N2 for 30 minutes, cooled to room temperature and extracted with EtOAc (2×50 mL). The organic layers were combined, washed with saturated NaHCO3 (50 mL) and brine (50 mL), dried over Na2SO4. Purification through silica gel column with 10-30% EtOAc/hexanes led to the product as yellow solid. Yield: 33 mg, 40%.

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc (2×50 mL)
  3. washwashed with saturated NaHCO3 (50 mL) and brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. customPurification through silica gel column with 10-30% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-aadd9604ff304cf5bcfa0cfedf43042e
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865682B2

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