Sodium Cyanide → 3,5-Dimethyl-4-(3'-iso-propyl-4'-methoxyphenoxy)phenylacetonitrile

HRID 2108628노트

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HRID 2108628 반응식
[C-:1]#[N:2].[Na+].[CH3:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([CH3:25])[C:12]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([CH:22]([CH3:24])[CH3:23])[CH:15]=1)[CH2:8]Br>O.C(O)C>[CH3:4][C:5]1[CH:6]=[C:7]([CH2:8][C:1]#[N:2])[CH:10]=[C:11]([CH3:25])[C:12]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([CH:22]([CH3:24])[CH3:23])[CH:15]=1

참가 물질

5

반응물 2

HCID 8929Sodium CyanideHCID 251495073,5-Dimethyl-4-(3'-iso-propyl-4'-methoxyphenoxy)benzyl bromide

생성물 1

HCID 666428163,5-Dimethyl-4-(3'-iso-propyl-4'-methoxyphenoxy)phenylacetonitrile수율 88.4%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

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온도
80 °C

실험 절차

To a stirred solution of sodium cyanide (0.23 g, 4.69 mmol) in H2O (2 mL) at room temperature was added a solution of 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxyphenoxy)benzyl bromide (0.85 g, 2.34 mmol) in ethanol (5 mL). The reaction mixture was heated at 80° C. for 2 h, cooled to room temperature, and poured into ice water (100 mL). The mixture was stirred for 1 h and extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with ethyl acetate-hexanes (1:4) to afford 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxyphenoxy)phenyl-acetonitrile as a brown solid (0.64 g, 85%, m.p.: 56-58° C.): 1H NMR (300 MHz, CDCl3): δ 7.07 (s, 2 H), 6.78 (d, J=3.3 Hz, 1 H), 6.68 (d, J=9.0 Hz, 1H), 6.35 (dd, J=3.0, 8.7 Hz, 1 H), 3.80 (s, 3 H), 3.73 (s, 2 H), 3.40-3.25 (m, 1 H), 2.16 (s, 6 H), 1.19 (d, J=7.2 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; mobile phase=ethyl acetate-hexanes (1:4); Rf=0.5.

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel
  8. washeluting with ethyl acetate-hexanes (1:4)

출처 및 근거

ORD 기록
ord-603b5ea9f4ca4f03b60040f9bdf0bbeb
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514419B2

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