Triethylamine → 4-Phenyl-2-pyridinecarbonitrile

HRID 1584008

反応式

HRID 1584008 の反応式
[C:1]1([C:7]2[CH:12]=[CH:11][N+:10]([O-])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]([N:16](CC)CC)C.C[Si](C#N)(C)C>C(#N)C>[C:14]([C:11]1[CH:12]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=[CH:9][N:10]=1)#[N:16]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 708034-Phenylpyridine-1-oxideHCID 82115Trimethylsilyl cyanide

生成物 1

HCID 877584-Phenyl-2-pyridinecarbonitrile

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 1.90 g (11.1 mmol) of 4-phenylpyridine-N-oxide (available from Aldrich Chemical Co.), 4.8 ml (35 mmol) of sieve-dried triethylamine and 4.7 ml (35 mmol) trimethylsilylcyanide in 10 ml of sieve-dried acetonitrile was heated to 100° for 24 hours. The reaction mixture was cooled, quenched with 1 ml of H2O then added to 50 ml of H2O and extracted with three-25 ml portions of ethyl acetate. The organic extracts were combined, dried (MgSO4), concentrated in vacuo and purified by flash chromatography (silica gel, 1:4 EtOAc/petroleum ether) to give 2-cyano-4-phenylpyridine as a white solid. Recrystallization (EtOAc/petroleum ether) of the solid afforded 1.65 g (83%) of title nitrile as white crystals, m.p. 97°-98°.

後処理

  1. temperatureThe reaction mixture was cooled
  2. customquenched with 1 ml of H2O
  3. additionthen added to 50 ml of H2O
  4. extractionextracted with three-25 ml portions of ethyl acetate
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography (silica gel, 1:4 EtOAc/petroleum ether)

出典と根拠

ORDレコード
ord-dce9f8a8f92d4bb09de767a3405114d7
出典データセット
uspto-grants-1985_11
特許番号
US04555520

関連ノート

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