Lithium hydroxide, monohydrate → 1216002-44-6

HRID 1098586Notes

Reaction equation

HRID 1098586 reaction equation
[C:1]([C:5]1[O:6][C:7]([C:10]([O:12]CC)=[O:11])=[CH:8][N:9]=1)([CH3:4])([CH3:3])[CH3:2].O[Li].O>C1COCC1.CCO.O>[C:1]([C:5]1[O:6][C:7]([C:10]([OH:12])=[O:11])=[CH:8][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66728774HCID 66728774, compound

Product 1

HCID 667288781216002-44-6Yield 78.1%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

To a stirring suspension of ethyl 2-tert-butyloxazole-5-carboxylate (1.0 g, 5.07 mmol) in 1:1:1 THF/EtOH/H2O (15 ml) at RT was added LiOH.H2O (486 mg) and the mixture was stirred at RT for 3 hours. The reaction mixture was checked by LC-MS and the completed reaction was concentrated to an aqueous residue, acidified (pH 3-4) with 3M HCl and extracted with EtOAc (3×). The combined organics were washed with brine (1×), dried (MgSO4) and evaporated to afford desired product, 2-tert-butyloxazole-5-carboxylic acid (0.67 g, 78% yield). 1H NMR (400 MHz, DMSO-d6): δ 12.9 (brs, 1H), 8.62 (s, 1H), 1.30 (s, 9H); (ESI) m/z: 170.0 (M+H+).

Workup

  1. customthe completed reaction
  2. concentrationwas concentrated to an aqueous residue
  3. extractionextracted with EtOAc (3×)
  4. washThe combined organics were washed with brine (1×)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-635dbf7eb46641f48030b6a1c187bbad
Source dataset
uspto-grants-2012_03
Patent number
US08143293B2

Reaction notes

Loading…