2-(4-Fluorophenyl)-N-methoxy-N-methylacetamide → 1-(4-Fluorophenyl)but-3-en-2-one

HRID 1991354ノート

反応式

HRID 1991354 の反応式
[CH:1]([Mg]Br)=[CH2:2].[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](N(OC)C)=[O:14])=[CH:8][CH:7]=1>C1COCC1.CCOCC.[Cl-].[Na+].O>[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](=[O:14])[CH:1]=[CH2:2])=[CH:8][CH:7]=1

参加物

6

反応物 2

HCID 210993112-(4-Fluorophenyl)-N-methoxy-N-methylacetamideHCID 178418507HCID 178418507、化合物

生成物 1

HCID 210992911-(4-Fluorophenyl)but-3-en-2-one収率 81.1%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
0 °C

実験手順

To a solution of 220 mL (1.0 M, 220 mmol) of vinylmagnesium bromide in 100 mL THF, was added dropwise under nitrogen atmosphere at 0° C. a solution of 21 g (106.6 mmol) 2-(4-fluoro-phenyl)-N-methoxy-N-methylacetamide (step A) in ˜150 mL dry ether. The reaction mixture was stirred at 0° C. for 0.5 hr then poured slowly into an ice/2N aq HCl mixture. The resulting mixture was diluted with ether and brine, transferred to a separatory funnel and the organic layer separated. The organic layer was washed with brine, dried over drying agent, filtered and the solvent evaporated under vacuum to give 14.2 g of the crude title compound which was used without further purification. 1H-NMR (CDCl3): δ: 7.19 (2H, m), 7.02 (2H, t, J=9.5 Hz), 6.42 (1H, dd, J1=14.2 Hz, J2=11 Hz). 6.34 (1H, d, J=14.2 Hz), 5.86 (1H, d, J=11 Hz), 3.87 (2H, s).

後処理

  1. customtransferred to a separatory funnel
  2. customthe organic layer separated
  3. washThe organic layer was washed with brine
  4. customdried
  5. customover drying agent
  6. filtrationfiltered
  7. customthe solvent evaporated under vacuum

出典と根拠

ORDレコード
ord-055b77453d504b43b051f9058f5951b1
出典データセット
uspto-grants-2010_01
特許番号
US07645790B2

反応ノート

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