Potassium Hydroxide → HCID 11603467, compound

HRID 2110879Notes

Reaction equation

HRID 2110879 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH:11]=[C:12]([CH:27]=[CH:28][CH:29]=2)[CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([O:25]C)=[O:24])=[CH:17][CH:16]=2)=[CH:2]1.[OH-].[K+]>O1CCCC1.C(O)C.C(OCC)(=O)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH:11]=[C:12]([CH:27]=[CH:28][CH:29]=2)[CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:17][CH:16]=2)=[CH:2]1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 23159874HCID 23159874, compound

Product 1

HCID 11603467HCID 11603467, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 3-(4-{[3-(1-benzothiophen-3-yl)benzyl]oxy}phenyl)propanoate (0.80 g, 1.99 mmol) was dissolved in a mixed solvent of tetrahydrofuran (10 mL) and ethanol (10 mL). An aqueous solution (5 mL) of 85% potassium hydroxide (0.28 g, 4.24 mmol) was added to the solution, 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 obtained crystals were washed with diethyl ether-hexane to give the title compound (0.70 g, yield 91%) as colorless prism crystals. MS: m/z 371 (M−OH), 1H NMR (CDCl3) δ: 2.65 (2H, t, J=7.4 Hz), 2.92 (2H, t, J=7.4 Hz), 5.13 (2H, s), 6.93 (2H, d, J=8.8 Hz), 7.14 (2H, d, J=8.8 Hz), 7.34-7.98 (9H, m).

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
  4. washThe obtained crystals were washed with diethyl ether-hexane

Sources & evidence

ORD record
ord-09ea1d48313940e9878add72ef799723
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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