Piperidine → HCID 22481729, 화합물

HRID 2181655노트

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HRID 2181655 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1I)[C:5]([O:7][CH3:8])=[O:6].[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])[CH2:17][CH3:18])[CH3:14].N1CCCCC1>CN(C=O)C.CCOC(C)=O.[Cu](I)I>[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])[C:17]1[O:1][C:2]2[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=[CH:10][C:11]=2[CH:18]=1)[CH3:14]

참가 물질

7

반응물 3

HCID 8082PiperidineHCID 20858Propane, 1,1-diethoxy-HCID 10378812Methyl 3-hydroxy-4-iodobenzoate

생성물 1

HCID 22481729HCID 22481729, 화합물수율 32.2%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
45 °C

실험 절차

A dried flask under nitrogen is charged with methyl 3-hydroxy-4-iodobenzoate (10.0 g, 35.9 mmol), propioaldehyde diethyl acetal (5.72 ml, 40.0 mmol), bistriphenylphosphine palladium diacetate (538 mg, 0.72 mmol), copper iodide (273 mg, 1.4 mmol) and piperidine (3.94 ml, 40.0 mmol) in DMF (50 ml). The mixture is stirred at 45° C. for 6 h, then at RT overnight. The reaction is diluted with EtOAc (250 ml) and washed with 50% saturated 1:1 NaCl/NaHCO3 solution (4×100 ml). The organic layer is dried (Na2SO4), filtered and concentrated to a brown oil. The crude material is chromatographed over 500 g slurry-packed silica, eluting with 15% EtOAc/hexane. The appropriate fractions are collected and concentrated, affording 3.22 g (32%) of methyl 2-(diethoxymethyl)-1-benzofuran-6-carboxylate as an orange oil. 1H NMR (400 MHz, CDCl3): δ 1.29, 3.72, 3.96, 5.70, 6.88, 7.61, 7.95, 8.20 ppm.

후처리

  1. customat RT
  2. customovernight
  3. washwashed with 50% saturated 1:1 NaCl/NaHCO3 solution (4×100 ml)
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a brown oil
  7. customThe crude material is chromatographed over 500 g slurry-packed silica
  8. washeluting with 15% EtOAc/hexane
  9. customThe appropriate fractions are collected
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4d3df3074ac249668a6cfe8c21477e0e
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06894042B2

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