Sodium Carbonate → 5-Ethynyl-4-(4-fluoro-phenyl)-1-methyl-1H-[1,2,3]triazole

HRID 402421ノート

反応式

HRID 402421 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[N:11][N:10]([CH3:13])[C:9]=2[CH:14]=O)=[CH:4][CH:3]=1.[C:16](=O)([O-])[O-].[K+].[K+].COP(C(=[N+]=[N-])C(=O)C)(=O)OC.C(=O)([O-])[O-].[Na+].[Na+]>CO>[C:14]([C:9]1[N:10]([CH3:13])[N:11]=[N:12][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)#[CH:16]

参加物

6

反応物 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 866647645-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]-triazole-4-carbaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

生成物 1

HCID 866647655-Ethynyl-4-(4-fluoro-phenyl)-1-methyl-1H-[1,2,3]triazole収率 92.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

To a mixture of 5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazole-4-carbaldehyde (616 mg, 3.0 mmol) in MeOH (13 mL) was added potassium carbonate (829 mg, 6.0 mmol) followed by a solution of (1-diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (634 mg, 3.3 mmol) in MeOH (4 mL) at room temperature and the resulting mixture stirred for 1 h. The mixture was then poured into sodium carbonate solution (1 M) and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 50% ethyl acetate in heptane) afforded the title compound (556 mg, 92%) as a light red solid. MS: m/e=202.2 [M]+.

後処理

  1. extractionextracted with ethyl acetate
  2. washthe combined organic extracts washed with brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by chromatography (silica, 0 to 50% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-8bf8c5759e0e43888ef37fa509d447f7
出典データセット
uspto-grants-2014_06
特許番号
US08742097B2

反応ノート

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