Methanol → 5-Ethynyl-2-methoxybenzonitrile

HRID 2240941ノート

反応式

HRID 2240941 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 534292965-Ethynyl-2-methoxybenzonitrile収率 69.2%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-1c26da37cfb643798614632de82e66c7
出典データセット
uspto-grants-2010_05
特許番号
US07723368B2

反応ノート

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