2,3-Dihydrofuran → 2-(3,4,5-Trimethoxyphenyl)-2,3-dihydrofuran

HRID 252771

반응식

HRID 252771 반응식
I[C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[C:6]([O:8][CH3:9])[CH:7]=1.[O:14]1[CH:18]=[CH:17][CH2:16][CH2:15]1.CC([O-])=O.[K+]>CN(C=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].CCOC(C)=O.O.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:9][O:8][C:6]1[CH:7]=[C:2]([CH:18]2[CH2:17][CH:16]=[CH:15][O:14]2)[CH:3]=[C:4]([O:12][CH3:13])[C:5]=1[O:10][CH3:11]

참가 물질

10

반응물 3

HCID 709342,3-DihydrofuranHCID 2981335-Iodo-1,2,3-trimethoxybenzeneHCID 517044Potassium Acetate

생성물 1

HCID 224789522-(3,4,5-Trimethoxyphenyl)-2,3-dihydrofuran수율 43.1%

시약·촉매·용매 6

HCID 11776Triphenylphosphine촉매HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

To a solution of 5-iodo-1,2,3-trimethoxybenzene (900 mg, 3.06 mmol) and 2,3-dihydrofuran (1.16 mL, 15.3 mmol) in dry DMF (8 mL) were added PPh3 (20 mg, 0.077 mmol), KOAc (901 mg, 9.18 mmol), n-Bu4NCl (850 mg, 3.06 mmol) and Pd(OAc)2 (17 mg, 0.077 mmol). The reaction mixture was stirred 18 h at 80° C. The reaction mixture was diluted with AcOEt and water. After separation, the organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude residue was then purified by flash chromatography on silica gel (AcOEt/Hexane: 20/80) to afford the title compound 287 (311 mg, 1.32 mmol, 43% yield). 1H NMR: (300 MHz, CDCl3) δ (ppm): 6.59 (s, 2H), 6.45 (m, 1H), 5.45 (dd, J=10.5, 8.4 Hz, 1H), 4.97 (m, 1H), 3.87 (s, 6H), 3.84 (s, 3H), 3.06 (m, 1H), 2.62 (m, 1H).

후처리

  1. customAfter separation
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was then purified by flash chromatography on silica gel (AcOEt/Hexane: 20/80)

출처 및 근거

ORD 기록
ord-a67bdf6bf52946058e0828fd58bfd8d7
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868204B2

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