Triethylamine → Methyl 2-((trimethylsilyl)ethynyl)benzoate

HRID 424795

반응식

HRID 424795 반응식
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1I.[CH3:12][Si:13]([C:16]#[CH:17])([CH3:15])[CH3:14].C(N(CC)CC)C>CN(C=O)C.[Cu]I>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:17]#[C:16][Si:13]([CH3:15])([CH3:14])[CH3:12]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 69132Benzoic acid, 2-iodo-, methyl ester

생성물 1

HCID 11053512Methyl 2-((trimethylsilyl)ethynyl)benzoate수율 85.1%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a solution of 2-iodo-benzoic acid methyl ester (792 mg, 3.02 mmol) in DMF (10 mL) are added trimethylsilylacetylene (854 μL, 6.04 mmol) and triethylamine (2.95 mL, 21.1 mmol). The reaction mixture is degassed for 20 minutes with a stream of nitrogen. Dichloro(bistriphenylphosphene) palladium (II) (212 mg, 0.302 mmol, 10 mol %) and copper (I) iodide (58 mg, 0.302 mmol, 10 mol %) are added and the reaction is heated to 80° C. After 3 h, the reaction is concentrated and the residue is chromatographed eluting with 0 to 5% EtOAc/Hexanes to yield the title compound (597 mg, 85%). GC/MS: 232.

후처리

  1. customThe reaction mixture is degassed for 20 minutes with a stream of nitrogen
  2. concentrationthe reaction is concentrated
  3. customthe residue is chromatographed
  4. washeluting with 0 to 5% EtOAc/Hexanes

출처 및 근거

ORD 기록
ord-b3cb5dace8cb4b3cb449666ab2002aaa
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106077B2

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