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

HRID 2380354Notes

Reaction equation

HRID 2380354 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 recrystallisation 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)
  3. customby recrystallisation in an n-hexane-ethyl acetate (2-1) mixture (40 cc), white crystals (m.p.=119°-120° C.)

Sources & evidence

ORD record
ord-fbaf54f3fff84a4fae28926f8847d678
Source dataset
uspto-grants-1994_11
Patent number
US05366982

Reaction notes

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