Sodium Hydroxide → HCID 23697867, compound

HRID 1609913Notes

Reaction equation

HRID 1609913 reaction equation
[CH3:1][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:22][CH:23]=2)=[CH:12][CH:11]=1)([CH3:8])[C:3]([O:5]CC)=[O:4].[OH-].[Na+:31]>CO>[CH3:8][C:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:22][CH:23]=2)=[CH:14][CH:15]=1)([CH3:1])[C:3]([O-:5])=[O:4].[Na+:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23590013HCID 23590013, compound

Product 1

HCID 23697867HCID 23697867, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Methyl-2-{4-[2-(2-phenyloxazol-4-yl)ethoxy]phenoxy}-propionic acid, ethyl ester 2.5 g, 63.2 mmol) was dissolved in MeOH (200 mL) and 2N NaOH (100 mL) was added. The resulting cloudy solution became clear after 30 min and the reaction was stirred vigorously for 6 h. The solvents were removed, and the residual solids were triturated with water. The suspended solids were then collected and triturated with pentane to produce a white solid (2.38 g, 97%). mp 199-200° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.90-7.93 (m, 2H), 7.46-7.49 (m, 3H), 6.73 (d, J=9.0 Hz, 2H), 6.69 (d, J=9.0 Hz, 2H), 4.12 (t, J=6.4 Hz, 2H), 2.91 (t, J=6.4 Hz, 2H), 1.26 (s, 3H); MS(EI): 390 (M+H), 366 (M−Na).

Workup

  1. customThe solvents were removed
  2. customthe residual solids were triturated with water
  3. customThe suspended solids were then collected
  4. customtriturated with pentane

Sources & evidence

ORD record
ord-1956f0619dfb413a86678117fd0cdf99
Source dataset
uspto-grants-2006_01
Patent number
US06982278B2

Reaction notes

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