Benzoic Acid → 4-(3,4,5-Trifluorophenyl)aminotetrahydropyran

HRID 561179ノート

反応式

HRID 561179 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:10])[C:8]=1[F:9])[NH2:5].[O:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1.C(O)(=O)C1C=CC=CC=1.[Na].[BH4-].[Na+]>>[F:1][C:2]1[CH:3]=[C:4]([NH:5][CH:14]2[CH2:15][CH2:16][O:11][CH2:12][CH2:13]2)[CH:6]=[C:7]([F:10])[C:8]=1[F:9]

参加物

5

反応物 4

HCID 243Benzoic AcidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 27249913,4,5-TrifluoroanilineHCID 131729286sodium NaBH4

生成物 1

HCID 590029984-(3,4,5-Trifluorophenyl)aminotetrahydropyran収率 41.4%

実験手順

To a mixture of 3,4,5-trifluoroaniline (3.70 g, 25.1 mmol), tetrahydro-4H-pyran-4-one (2.52 g, 25.1 mmol), and benzoic acid (3.07 g, 25.1 mmol), was added sodium NaBH4 (0.95 g, 25.1 mmol), the whole mixture was stirred at room temperature for 1.5 h. After quenching with the reaction mixture with 1 M aq. NaOH under cooling with ice, the whole mixture was extracted with Et2O. The extract was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Flash chromatography of the residue (hexane:EtOAc=3:2) gave 4-(3,4,5-trifluorophenyl)aminotetrahydropyran (2.40 g, 41%) as a white powder.

後処理

  1. customAfter quenching with the reaction mixture with 1 M aq. NaOH
  2. temperatureunder cooling with ice
  3. extractionthe whole mixture was extracted with Et2O
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e742700a7c074932902206bbe5236fda
出典データセット
uspto-grants-2011_11
特許番号
US08063221B2

反応ノート

読み込み中…