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

HRID 252771

反応式

HRID 252771 の反応式
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]

参加物

10

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 6

HCID 11776Triphenylphosphine触媒HCID 70681Tetrabutylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a67bdf6bf52946058e0828fd58bfd8d7
出典データセット
uspto-grants-2011_01
特許番号
US07868204B2

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