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

HRID 333363

反応式

HRID 333363 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 66133Benzyl triethylammonium chloride触媒HCID 178418476HCID 178418476、化合物触媒HCID 22272177Toluene water溶媒

反応条件

温度
50 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-7bf0b10118034bb1bb14191273d87519
出典データセット
uspto-grants-2014_11
特許番号
US08877923B2

関連ノート

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