Sodium Hydroxide → HCID 10977715, compound

HRID 1393469Notes

Reaction equation

HRID 1393469 reaction equation
C[O:2][C:3](=[O:19])[CH2:4][C:5]1[N:6]=[C:7]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:8][C:9]=1[CH3:10].[OH-].[Na+]>CO>[CH3:10][C:9]1[O:8][C:7]([CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[N:6][C:5]=1[CH2:4][C:3]([OH:19])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10999783HCID 10999783, compound

Product 1

HCID 10977715HCID 10977715, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

(5-Methyl-2-phenethyl-oxazol-4-yl)-acetic acid methyl ester (8.75 g, 33.8 mmol), in MeOH (120 mL) was treated with 5N NaOH (40 mL) and then the solution was warmed to 40° C. After 40 min, the reaction mixture was concentrated under reduced pressure, suspended in water, and then acidified to pH=1 with 5N HCl. The mixture was extracted with EtOAc (2×), dried (MgSO4), and concentrated to provide 5.25 g (63%) of the product as an off-white solid. 1H NMR (400 MHz, CDCl3) ••1H NMR (400 MHz, CDCl3) δ 7.33-7.20 (m, 5H), 3.52 (s, 2H), 3.06-3.03 (m, 4H), 2.24 (s, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. extractionThe mixture was extracted with EtOAc (2×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-14bf6bf1d6b04797ad6798d7ed8c6caf
Source dataset
uspto-grants-2008_03
Patent number
US07345070B2

Reaction notes

Loading…