Potassium Hydroxide → 2-Ethyl-2-methyl-6-[(4,6-diphenyl-2-pyridyl)oxy]hexanoic acid

HRID 2396531

Reaction equation

HRID 2396531 reaction equation
[CH2:1]([C:3]([CH3:32])([CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=[C:16]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:15]=1)[C:4]([O:6]CC)=[O:5])[CH3:2].[OH-].[K+]>O.C(O)C>[CH2:1]([C:3]([CH3:32])([CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=[C:16]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:15]=1)[C:4]([OH:6])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 18987342Ethyl 2-ethyl-2-methyl-6-[(4,6-diphenyl-2-pyridyl)oxy]hexanoate

Product 1

HCID 189872252-Ethyl-2-methyl-6-[(4,6-diphenyl-2-pyridyl)oxy]hexanoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The procedure in Example 6 is followed but using ethyl 2-ethyl-2-methyl-6-[(4,6-diphenyl-2-pyridyl)oxy]hexanoate (3.6 g), potassium hydroxide pellets (0.95 g) dissolved in distilled water (20 cc) and ethanol (50 cc). The reaction mixture is refluxed for 120 hours. The product is purified by chromatography under pressure on silica gel (30-60 mm; eluent: n-hexane-ethyl acetate 75-25) and then by recrystaliisation in an n-hexane-ethyl acetate (2-1) mixture (40 cc), white crystals (m.p.=119°-120° C.)

Workup

  1. temperatureThe reaction mixture is refluxed for 120 hours
  2. customThe product is purified by chromatography under pressure on silica gel (30-60 mm; eluent: n-hexane-ethyl acetate 75-25)

Sources & evidence

ORD record
ord-8da2742e27274cefa683013725d9a8e2
Source dataset
uspto-grants-1996_02
Patent number
US05492915

Linked notes

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