Hydrochloric Acid → HCID 22241398, compound

HRID 892194Notes

Reaction equation

HRID 892194 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:13]=[C:14]([O:18]C(=O)C3C=CC=CC=3)[CH:15]=[CH:16][CH:17]=2)=[N:7][CH:8]=1)[CH3:2].C1COCC1.CO.[OH-].[Na+].Cl>CCOC(C)=O.O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=2)=[N:7][CH:8]=1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 54568744Benzoic acid 3-[2-(5-ethyl-pyridin-2-yl)-ethoxy]-phenyl ester

Product 1

HCID 22241398HCID 22241398, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of benzoic acid 3-[2-(5-ethyl-pyridin-2-yl)-ethoxy]-phenyl ester (493 mg, 1.42 mmol, example 70) in 1:1 THF/CH3OH (5 mL) is added 10N NaOH soln. (0.5 mL) and water (50 μL). The reaction mixture is stirred for 15 min then cooled to 5° C., adjusted to pH 7 with 2N HCl soln. and diluted with EtOAc. The organic layer is washed sequentially with brine, sat NaHCO3 soln. then dried over MgSO4 and concentrated. The residue is purified by several triturations with hexane to give the title compound as a crystalline solid. MS (ESI) 244 (M+H)+.

Workup

  1. washThe organic layer is washed sequentially with brine
  2. dry with materialthen dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue is purified by several triturations with hexane

Sources & evidence

ORD record
ord-3007aad145f047199f5077a807d6fe21
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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