Tetrahydrofuran → HCID 23159928, compound

HRID 2110881Notes

Reaction equation

HRID 2110881 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[CH:11]=[C:12]([CH:26]=[CH:27][CH:28]=3)[CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:17][CH:16]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.O1CCC[CH2:30]1>C(OCC)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[CH:11]=[C:12]([CH:26]=[CH:27][CH:28]=3)[CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([O:25][CH3:30])=[O:24])=[CH:17][CH:16]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 23159897HCID 23159897, compound

Product 1

HCID 23159928HCID 23159928, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(4-{[3-(1H-indol-5-yl)benzyl]oxy}phenyl)propanoic acid (1.0 g, 2.69 mmol) in tetrahydrofuran (30 mL) was added a 2 mol/L trimethylsilyldiazomethane diethyl ether solution (1.5 mL, 3.0 mmol), and the mixture was stirred at room temperature for 18 hr. The reaction solution was diluted with ethyl acetate, and the mixture washed successively with aqueous citric acid solution, water and aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:5-1:3-1:2) to give the title compound (0.90 g, yield 86%) as a pale-yellow oil.

Workup

  1. washthe mixture washed successively with aqueous citric acid solution, water and aqueous sodium chloride solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-76df195a84564b87949251f1ab6358cc
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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