Hydrochloric Acid → 2-(4-Methoxyphenyl)-2-methylpropanenitrile

HRID 228164

反応式

HRID 228164 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[K+].F[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.[C:20](#[N:24])[CH:21]([CH3:23])[CH3:22].Cl>O1CCCC1>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:21]([CH3:23])([CH3:22])[C:20]#[N:24])=[CH:13][CH:14]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6559IsobutyronitrileHCID 99874-FluoroanisoleHCID 3251421Potassium bis(trimethylsilyl)amide

生成物 1

HCID 2191662-(4-Methoxyphenyl)-2-methylpropanenitrile収率 52%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Add potassium bis(trimethylsilyl)amide (39.90 g, 200 mmol) to a stirred solution of 4-fluoroanisole (15.0 mL, 133 mmol), isobutyronitrile (49.0 mL, 539 mmol) and anhydrous tetrahydrofuran (150 mL). Heat the reaction to reflux under nitrogen for 72 h. Cool the reaction to room temperature, pour it into 1 N hydrochloric acid (300 mL), and extract with diethyl ether (3×100 mL). Wash the diethyl ether extracts with brine (100 mL), dry the extracts over magnesium sulfate, filter, and concentrate on a rotary evaporator to give the crude product. The crude product is purified by flash chromatography on silica gel eluting with 10% ethyl acetate/hexanes to yield 12.13 g (52%) of 2-(4-methoxy-phenyl)-2-methyl-propionitrile: TLC: Rf in 10% ethyl acetate/hexanes: 0.30; 1H NMR (CDCl3): 7.40-7.37 (m, 2H), 6.92-6.90 (m, 2H), 3.81 (s, 3H), 1.70 (s, 6H).

後処理

  1. temperatureHeat
  2. customthe reaction
  3. temperatureto reflux under nitrogen for 72 h
  4. temperatureCool
  5. customthe reaction to room temperature
  6. extractionextract with diethyl ether (3×100 mL)
  7. washWash the diethyl ether
  8. dry with materialdry the extracts over magnesium sulfate
  9. filtrationfilter
  10. concentrationconcentrate on a rotary evaporator
  11. customto give the crude product
  12. customThe crude product is purified by flash chromatography on silica gel eluting with 10% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-f3dcd6e3ee9947f6902923fb0c4cec45
出典データセット
uspto-grants-2009_07
特許番号
US07560463B2

関連ノート

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