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

HRID 130707

반응식

HRID 130707 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 2191662-(4-Methoxyphenyl)-2-methylpropanenitrile수율 52%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ccf243a42fc24f19b931160a3d67fead
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381719B2

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