1-Methoxybuta-1,3-diene → 4-{2-[(e)-2-Methoxyethenyl]-2,3-dihydro-1-benzofuran-5-yl}benzonitrile

HRID 494814

반응식

HRID 494814 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1I.[CH3:17][O:18][CH:19]=[CH:20][CH:21]=[CH2:22].C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C(Cl)Cl.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:17][O:18]/[CH:19]=[CH:20]/[CH:21]1[CH2:22][C:3]2[CH:4]=[C:5]([C:8]3[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=3)[CH:6]=[CH:7][C:2]=2[O:1]1

참가 물질

8

반응물 3

HCID 182131-Methoxybuta-1,3-dieneHCID 516892Sodium BicarbonateHCID 103586764-(4-Hydroxy-3-iodophenyl)benzonitrile

생성물 1

HCID 222746034-{2-[(e)-2-Methoxyethenyl]-2,3-dihydro-1-benzofuran-5-yl}benzonitrile수율 549.9%

시약·촉매·용매 4

HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

반응 조건

온도
23 °C

실험 절차

A solution of Example 1A (0.20 g, 0.623 mmol), 1-methoxybutadiene (0.18 g, 2.18 mmol), palladium diacetate (0.007 g, 0.031 mmol), sodium bicarbonate (0.261 g, 3.11 mmol) and tetrabutyl ammonium chloride (0.173 g, 0.623 mmol) was heated at 60° C. in DMF (3 mL) under an atmosphere of nitrogen for 36 hours. The reaction was cooled to 23° C., diluted with CH2Cl2 (50 mL), filtered through Celite. The solution was concentrated under reduce pressure and the residue was purified on silica using CH2Cl2 to give the titled compound (0.95 g, 55%). 1HNMR (CDCl3): 3.05 (m, 1H), 3.40 (m, 1H), 3.60 (s, 3H), 5.00 (m, 1H), 5.22 (m, 1H), 6.72 (d, J=14 Hz, 1H), 6.83 (d, J=7 Hz, 1H), 7.38 (m, 2H), 7.65 (m, 4H); MS (DCI): 278 (M+H+), 295 (M+NH4+).

후처리

  1. filtrationfiltered through Celite
  2. concentrationThe solution was concentrated
  3. customthe residue was purified on silica

출처 및 근거

ORD 기록
ord-4ff6943717344cc6a31885b631682cf6
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538138B2

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