Cesium carbonate → 6-(4-Fluoro-2-methylphenoxy)-1,2,3,4-tetrahydronaphthalen-1-one

HRID 63629

反応式

HRID 63629 の反応式
Br[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.[F:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([CH3:21])[CH:15]=1.N1C=CC=CC=1CC(C)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.O>[F:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][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)=[C:16]([CH3:21])[CH:15]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 959101-(Pyridin-2-yl)propan-2-oneHCID 1362954-Fluoro-2-methylphenolHCID 101050696-Bromo-1-tetralone

生成物 1

HCID 1185981606-(4-Fluoro-2-methylphenoxy)-1,2,3,4-tetrahydronaphthalen-1-one収率 95.6%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

To a suspension of 6-bromo-1,2,3,4-tetrahydronaphthalen-1-one (2.0 g, 8.9 mmol), 4-fluoro-2-methylphenol (1.7 g, 13.3 mmol), 1-pyridin-2-ylacetone (240 mg, 1.8 mmol) and Cs2CO3 (5.8 g, 17.8 mmol) in DMSO (40 mL) was added CuBr (127 mg, 0.9 mmol) at rt under N2. The reaction was stirred at 100° C. overnight. The reaction was cooled, diluted with water (50 mL), and extracted with EtOAc (3×50 mL). Organics were washed with water (3×50 mL) and brine (50 mL), dried (Na2SO4), and concentrated. Purification by silica gel chromatography (PE:EtOAc=30:1) gave 2.3 g (95%) of the title compound as a colorless oil. [M+H] Calc'd for C17H15FO2, 271. Found, 271.

後処理

  1. temperatureThe reaction was cooled
  2. extractionextracted with EtOAc (3×50 mL)
  3. washOrganics were washed with water (3×50 mL) and brine (50 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (PE:EtOAc=30:1)

出典と根拠

ORDレコード
ord-1d69527dfb824fd28985ca2c6f39fa80
出典データセット
uspto-grants-2016_09
特許番号
US09447046B2

関連ノート

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