Triphenylphosphine → 4-[5-(3,4,5-Trimethoxy-phenyl)-2,5-dihydrofuran-2-yl]-benzoic Acid Ethyl Ester

HRID 1174601Notes

Reaction equation

HRID 1174601 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]2[CH2:17][CH:16]=[CH:15][O:14]2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH2:18]([O:20][C:21](=[O:29])[C:22]1[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=1)[CH3:19].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:18]([O:20][C:21](=[O:29])[C:22]1[CH:27]=[CH:26][C:25]([CH:15]2[CH:16]=[CH:17][CH:13]([C:5]3[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[O:14]2)=[CH:24][CH:23]=1)[CH3:19]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 142891Ethyl 4-iodobenzoateHCID 224789522-(3,4,5-Trimethoxyphenyl)-2,3-dihydrofuran

Product 1

HCID 207859344-[5-(3,4,5-Trimethoxy-phenyl)-2,5-dihydrofuran-2-yl]-benzoic Acid Ethyl EsterYield 86.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 287 (200 mg, 0.846 mmol) and 4-Iodo-benzoic acid ethyl ester (468 mg, 1.69 mmol) in dry acetonitrile (4 mL) were added PPh3 (20 mg, 0.076 mmol), Ag2CO3 (467 m 1.69 mmol) and Pd(OAc)2 (7 mg, 0.03 mmol). The reaction mixture was stirred 18 h at 80° C. The reaction mixture was filtered through celite and washed with AcOEt. Water was added and the phases were separated. 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: 30/70) to afford the title compound 288 (280 mg, 0.728 mmol, 86% yield). 1H NMR (300 MHz, CDCl3) δ (ppm): 8.05 (d, J=7.5 Hz, 2H), 7.45 (d, J=7.5 Hz, 2H), 6.61 (s, 2H), 6.18-5.95 (m, 4H), 4.38 (q, J=7.0 Hz, 2H, 3.88 (s, 6H), 3.84 (s, 3), 1.39 (t, J=7.0 Hz).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with AcOEt
  3. additionWater was added
  4. customthe phases were separated
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude residue was then purified by flash chromatography on silica gel (AcOEt/Hexane: 30/70)

Sources & evidence

ORD record
ord-06a477ead3244baa82401f0d68277f3f
Source dataset
uspto-grants-2010_11
Patent number
US07838520B2

Reaction notes

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