Methanol → 5-Ethynyl-2-methoxybenzonitrile

HRID 2240941노트

반응식

HRID 2240941 반응식
F[C:2]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][Si](C)(C)C)=[CH:6][C:3]=1[C:4]#[N:5].CO.[C:18](=O)([O-])[O-:19].[Cs+].[Cs+]>C(Cl)Cl.C(OCC)C>[C:10]([C:7]1[CH:8]=[CH:9][C:2]([O:19][CH3:18])=[C:3]([CH:6]=1)[C:4]#[N:5])#[CH:11]

참가 물질

6

반응물 3

HCID 887MethanolHCID 10796Cesium carbonateHCID 593053312-Fluoro-5-((trimethylsilyl)ethynyl)benzonitrile

생성물 1

HCID 534292965-Ethynyl-2-methoxybenzonitrile수율 69.2%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 2-Fluoro-5-trimethylsilanylethynyl-benzonitrile (0.935 g, 4.3 mmol), in dry methylene chloride (10 mL) and methanol (10 mL) was added cesium carbonate (1.7 g, 5.2 mmol) and stirred for 2 h under a nitrogen atmosphere. The mixture was diluted with diethyl ether (100 mL), and partitioned between diethyl ether and H2O (100 mL), and the aqueous layer was extracted with diethyl ether (50 mL), washed with brine and dried over MgSO4, filtered and concentrated in vacuo. Purification by flash chromatography (20-30% ethyl acetate/petroleum ether) gave the title compound as a tan solid (0.468 g, 69%), identified by NMR and mass spectral analyses. Mp: 100-101° C. MS (EI+): 157 (M+).

후처리

  1. custompartitioned between diethyl ether and H2O (100 mL)
  2. extractionthe aqueous layer was extracted with diethyl ether (50 mL)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (20-30% ethyl acetate/petroleum ether)

출처 및 근거

ORD 기록
ord-1c26da37cfb643798614632de82e66c7
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723368B2

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