Trimethylsilyldiazomethane → Methyl 4-cyano-2-ethoxybenzoate

HRID 2105831ノート

反応式

HRID 2105831 の反応式
[CH3:1][Si](C=[N+]=[N-])(C)C.[C:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[C:12]([O:19][CH2:20][CH3:21])[CH:11]=1)#[N:9]>C1C=CC=CC=1.CO>[C:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([O:16][CH3:1])=[O:15])=[C:12]([O:19][CH2:20][CH3:21])[CH:11]=1)#[N:9]

参加物

5

反応物 2

HCID 167693TrimethylsilyldiazomethaneHCID 226750384-Cyano-2-ethoxybenzoic acid

生成物 1

HCID 57809105Methyl 4-cyano-2-ethoxybenzoate収率 72.3%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 887Methanol溶媒

実験手順

(Trimethylsilyl)diazomethane (2 M in hexanes, 1.47 mL, 2.93 mmol) was added to a solution of 4-cyano-2-ethoxybenzoic acid (280 mg, 1.47 mmol) in benzene (8.0 mL) and methanol (1.6 mL). The reaction was stirred for 1 h and then degassed with air for 30 min. Evaporation of the solvent and purification of the crude residue by flash column chromatography (silica gel, eluting with 0-20% ethyl acetate in hexanes) gave methyl 4-cyano-2-ethoxybenzoate as a yellow solid (218 mg, 71%).

後処理

  1. customdegassed with air for 30 min
  2. customEvaporation of the solvent and purification of the crude residue
  3. washby flash column chromatography (silica gel, eluting with 0-20% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-412f143d7b93495ba41db8c247a39c92
出典データセット
uspto-grants-2009_08
特許番号
US07579368B2

反応ノート

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