Methanol → 7-Chloro-2-(fluoromethyl)-2-methylchroman-4-one

HRID 1913309ノート

反応式

HRID 1913309 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([OH:11])[CH:3]=1.CO.[F:14][CH2:15][C:16](=O)[CH3:17].N1CCCC1>CC(OC)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:8](=[O:10])[CH2:9][C:16]([CH2:15][F:14])([CH3:17])[O:11]2)=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 887MethanolHCID 9889FluoroacetoneHCID 31268PyrrolidineHCID 10515131-(4-Chloro-2-hydroxyphenyl)ethanone

生成物 1

HCID 673626587-Chloro-2-(fluoromethyl)-2-methylchroman-4-one収率 94.3%

試薬・触媒・溶媒 1

HCID 15413tert-Butyl methyl ether溶媒

実験手順

1-(4-Chloro-2-hydroxyphenyl)ethanone (10.2 g, 59.8 mmol), MeOH (100 mL), fluoroacetone (5.00 g, 65.8 mmol), and pyrrolidine (5.44 ml, 65.8 mmol) were stirred at ambient temperature. After 3 days, LCMS showed complete reaction. The reaction mixture was diluted with MTBE (250 mL), washed with water (100 mL), 2N HCl (2×50 mL), brine (50 mL), 2N NaOH (2×50 mL), and brine (2×50 mL). The organic portion was dried (Na2SO4), filtered, and concentrated to provide the title compound (12.9 g, 56.4 mmol, 94% yield) as a brown oil. MS (DCI/NH3) m/z 246 (M+NH4)+.

後処理

  1. customreaction
  2. washwashed with water (100 mL), 2N HCl (2×50 mL), brine (50 mL), 2N NaOH (2×50 mL), and brine (2×50 mL)
  3. dry with materialThe organic portion was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-92f2eb682fda4c6e8e0425b2f1cfe45c
出典データセット
uspto-grants-2013_12
特許番号
US08609692B2

反応ノート

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