Methanol → 2-(3-(Benzyloxy)-4-methoxyphenyl)acetonitrile

HRID 17946

반응식

HRID 17946 반응식
CC([O-])(C)C.[K+].CC1C=CC(S([CH2:17][N+:18]#[C-])(=O)=O)=CC=1.[CH2:20]([O:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[CH:31]=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CO>C1COCC1.O>[CH2:20]([O:27][C:28]1[CH:29]=[C:30]([CH2:31][C:17]#[N:18])[CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

7

반응물 4

HCID 887MethanolHCID 806713-Benzyloxy-4-methoxybenzaldehydeHCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxide

생성물 1

HCID 131316582-(3-(Benzyloxy)-4-methoxyphenyl)acetonitrile수율 48%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

실험 절차

To a suspension of t-BuOK (20.15 g, 0.165 mol) in THF (250 mL) was added a solution of TosMIC (16.1 g, 82.6 mmol) in THF (100 mL) at −78° C. The mixture was stirred for 15 minutes, treated with a solution of 3-benzyloxy-4-methoxy-benzaldehyde (10.0 g, 51.9 mmol) in THF (50 mL) dropwise, and continued to stir for 1.5 hours at −78° C. To the cooled reaction mixture was added methanol (50 mL). The mixture was heated at reflux for 30 minutes. Solvent of the reaction mixture was removed to give a crude product, which was dissolved in water (300 mL). The aqueous phase was extracted with EtOAc (100 mL×3). The combined organic layers were dried and evaporated under reduced pressure to give crude product, which was purified by column chromatography (Petroleum Ether/EtOAc 10:1) to afford 2-(3-(Benzyloxy)-4-methoxyphenyl)acetonitril (5.0 g, 48%). 1H NMR (300 MHz, CDCl3) δ 7.48-7.33 (m, 5H), 6.89-6.86 (m, 3H), 5.17 (s, 2H), 3.90 (s, 3H), 3.66 (s, 2H). 13C NMR (75 MHz, CDCl3) δ 149.6, 148.6, 136.8, 128.8, 128.8, 128.2, 127.5, 127.5, 122.1, 120.9, 118.2, 113.8, 112.2, 71.2, 56.2, 23.3.

후처리

  1. stirringto stir for 1.5 hours at −78° C
  2. customTo the cooled reaction mixture
  3. temperatureThe mixture was heated
  4. temperatureat reflux for 30 minutes
  5. customSolvent of the reaction mixture was removed
  6. customto give a crude product, which
  7. extractionThe aqueous phase was extracted with EtOAc (100 mL×3)
  8. customThe combined organic layers were dried
  9. customevaporated under reduced pressure
  10. customto give crude product, which
  11. customwas purified by column chromatography (Petroleum Ether/EtOAc 10:1)

출처 및 근거

ORD 기록
ord-63e7c4d2e9c044a7bc0aea04f6105f37
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741321B2

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