Potassium Carbonate → 6-{[6-(Trifluoromethyl)pyridin-2-yl]oxy}-1,2,3,4-tetrahydronaphthalen-1-one

HRID 63092

反応式

HRID 63092 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.Cl[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[F:21][C:20]([F:23])([F:22])[C:16]1[N:15]=[C:14]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]3)[CH:19]=[CH:18][CH:17]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 6023342-Chloro-6-(trifluoromethyl)pyridineHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

生成物 1

HCID 867282186-{[6-(Trifluoromethyl)pyridin-2-yl]oxy}-1,2,3,4-tetrahydronaphthalen-1-one収率 61.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
120 °C

実験手順

To a solution of 6-hydroxy-3,4-dihydro-1(2H)-naphthalenone (5.0 g, 30.8 mmol) and 2-chloro-6-(trifluoromethyl)pyridine (5.87 g, 32.3 mmol) in ACN (100 mL) was added potassium carbonate (6.39 g, 46.2 mmol), and the reaction was heated at 120° C. in a sealed vessel overnight. The reaction was cooled, diluted with water (100 mL), and extracted with EtOAc (100 mL×3). Organics were dried (Na2SO4), and concentrated. Purification by silica gel chromatography (10-80% EtOAc/hexanes) gave 5.8 g (61%) of the title compound as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 2.13-2.20 (2H, m), 2.67 (2H, t, J=6.2 Hz), 2.97 (2H, t, J=6.0 Hz), 7.07-7.14 (2H, m), 7.45 (1H, d, J=7.4 Hz), 7.89 (1H, t, J=8.0 Hz), 8.09 (1H, d, J=8.3 Hz). [M+H] calc'd for C16H12F3NO2, 308; found 308.

後処理

  1. temperatureThe reaction was cooled
  2. extractionextracted with EtOAc (100 mL×3)
  3. dry with materialOrganics were dried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (10-80% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-02a3a29fd893426a8ca65f2851ddf9d6
出典データセット
uspto-grants-2016_09
特許番号
US09447045B2

関連ノート

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