Potassium Carbonate → 4-(4-(2-Oxazolyl)phenoxy)benzaldehyde

HRID 16474

反応式

HRID 16474 の反応式
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.C([O-])([O-])=O.[K+].[K+].F[C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([O:12][C:20]2[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=2)=[CH:8][CH:7]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 516892Sodium BicarbonateHCID 1356214594-(Oxazol-2-yl)phenol

生成物 1

HCID 866134384-(4-(2-Oxazolyl)phenoxy)benzaldehyde収率 94.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-(2-oxazolyl)phenol (4.1 g, 25.44 mmol) in DMF (98 ml), K2CO3 (3.52 g, 25.44 mmol, 1 equiv.) was added. The reaction was stirred at ambient temperature for 30 min. Then, 4-fluorobenzaldehyde (2.73 mL, 25.44 mmol, 1 equiv., Aldrich # 12,837-6) was added and stirring was continued at 150° C. for 4 hours. After cooling, saturated NaHCO3 was added to the reaction mixture. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Flashmaster chromatography on 50 g of silica gel using a gradient of 100% hexane→50% hexane+50% ethyl acetate gave 6.4 g of 4-[4-(2-oxazolyl)phenoxy]benzaldehyde still containing 20 mol % DMF. Further drying led to the pure product (6.05 g; 90% th.; 148% pract.); 1H NMR (CDCl3) δ 9.95 (s, 1H), 8.09 (d, 2H), 7.89 (d, 2H), 7.72 (d, 1H), 7.24 (d, 1H), 7.16 (d, 2H), 7.13 (d, 2H) ppm.

後処理

  1. stirringstirring
  2. waitwas continued at 150° C. for 4 hours
  3. temperatureAfter cooling
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-459bf0305e284beaae1e3ca5b5ccc755
出典データセット
uspto-grants-2010_06
特許番号
US07737145B2

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