Tetrahydrofuran → 1-(2',4'-Dichloro-biphenyl-4-yl)-hex-5-en-1-one

HRID 227891

反応式

HRID 227891 の反応式
CON(C)[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])=[CH:8][CH:7]=1)=[O:5].[NH4+].[Cl-].C(O[CH2:27][CH3:28])(=O)C.O1C[CH2:32][CH2:31][CH2:30]1>>[Cl:19][C:13]1[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=1[C:9]1[CH:10]=[CH:11][C:6]([C:4](=[O:5])[CH2:30][CH2:31][CH2:32][CH:27]=[CH2:28])=[CH:7][CH:8]=1

参加物

5

反応物 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 577572372',4'-Dichloro-biphenyl-4-carboxylic acid methoxy-methyl-amide

生成物 1

HCID 577572631-(2',4'-Dichloro-biphenyl-4-yl)-hex-5-en-1-one

実験手順

5-Bromo-1-pentene (5 g) was gently heated with magnesium turnings (1 g) in anhydrous tetrahydrofuran (25 mL) until reaction started. The mixture was left to reflux without further heating to give the Grignard reagent, then allowed to cool to room temperature. 2′,4′-Dichloro-biphenyl-4-carboxylic acid methoxy-methyl-amide (2 g) was dissolved in anhydrous tetrahydrofuran (25 mL) and chilled in an ice bath. The above Grignard reagent was added dropwise with vigorous stirring. Following addition, the mixture was allowed to warm to room temperature and stirring continued for 2 hours. Saturated NH4Cl solution (50 mL) was added and the mixture extracted with petrol. Drying with Na2SO4 and evaporation gave an oil. Column chromatography (petrol:ethyl acetate) gave the title compound as a clear oil which solidified overnight. 13C NMR (CDCl3): δ 23.4, 33.3, 37.8, 115.3, 127.4, 128.0, 129.7, 129.9, 131.9, 133.1, 134.5, 136.3, 138.0, 138.4, 142.8 and 199.9. 1H NMR (CDCl3): δ 1.85 (2H, t, J=7.0 Hz), 2.18 (2H, t, J=7.0 Hz), 3.03 (2H, t, J=7.3 Hz), 5.01 (2H, m), 5.87 (1H, m), 7.28 (2H, d, J=8.2 Hz), 7.31 (1H, s), 7.52 (2H, m) and 8.00 (2H, m).

後処理

  1. temperaturechilled in an ice bath
  2. additionaddition
  3. temperatureto warm to room temperature
  4. extractionthe mixture extracted with petrol
  5. dry with materialDrying with Na2SO4 and evaporation
  6. customgave an oil

出典と根拠

ORDレコード
ord-b2b724ce34b0457ab6e44ed8c77bd662
出典データセット
uspto-grants-2009_07
特許番号
US07560597B2

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