Acetonitrile → HCID 53640530, 화합물

HRID 1824868노트

반응식

HRID 1824868 반응식
[OH-].[K+].[C:3]1(/[C:9](/[C:19]2[CH:24]=[CH:23][C:22]([CH:25]=O)=[CH:21][CH:20]=2)=[C:10](/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)\[CH2:11][CH3:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:27][C:28]#[N:29]>O>[C:3]1([C:9]([C:19]2[CH:24]=[CH:23][C:22]([CH:25]=[CH:27][C:28]#[N:29])=[CH:21][CH:20]=2)=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH3:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 14797Potassium HydroxideHCID 11723053HCID 11723053, 화합물

생성물 1

HCID 53640530HCID 53640530, 화합물수율 57%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A suspension of potassium hydroxide (85%, 260 mg, 3.9 mmol) in CH3CN (25 mL) was heated to reflux and (Z)-1,2-Diphenyl-1-(4-formylphenyl)-1-butene (4a) (Willson J. Med. Chem. 1994, 37, 1550–1552) (1.0 g, 3.18 mmol) was added in portions. After refluxing 5 min, the mixture was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine and dried (MgSO4). The solvent was removed under reduced pressure and the residue chromatographed (silica gel, 15% EtOAc/hexanes) to give nitrile (4b) as a white solid (616 mg, 57%): 1H NMR (CDCl3) δ 7.39–7.07 (m, 13H), 6.91 (d, J=8.4 Hz, 2H), 5.69 (d, J=16.9 Hz, 1H), 2.48 (q, J=7.3 Hz, 2H), 0.94 (t, J=7.3 Hz, 3H); HRMS calcd. for C25H21N (M+H+) 335.1674; found 335.1679.

후처리

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureAfter refluxing 5 min
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed under reduced pressure
  8. customthe residue chromatographed (silica gel, 15% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-fcf2e46f729d4c7baeda18b207c0e0dc
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07045540B2

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