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

HRID 402421노트

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HRID 402421 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-8bf8c5759e0e43888ef37fa509d447f7
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742097B2

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