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

HRID 2108628ノート

反応式

HRID 2108628 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-603b5ea9f4ca4f03b60040f9bdf0bbeb
出典データセット
uspto-grants-2009_04
特許番号
US07514419B2

反応ノート

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