Sodium Hydroxide → HCID 86714640, compound

HRID 1409363Notes

Reaction equation

HRID 1409363 reaction equation
[OH:1][CH:2]([C:6]1[O:10][N:9]=[C:8]([C:11]([O:13]CC)=[O:12])[CH:7]=1)[CH:3]([CH3:5])[CH3:4].[OH-].[Na+]>C(O)C>[OH:1][CH:2]([C:6]1[O:10][N:9]=[C:8]([C:11]([OH:13])=[O:12])[CH:7]=1)[CH:3]([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70980420HCID 70980420, compound

Product 1

HCID 86714640HCID 86714640, compoundYield 159.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 5-(1-hydroxy-2-methylpropyl)isoxazole-3-carboxylate (2.345 mmol, 0.5 g) was dissolved in ethanol (5 ml) and cooled to 0° C. NaOH 1 M solution (5 ml) was slowly added and the resulting mixture was allowed to warm to RT. The solution was heated to 60° C. for 3 h. Ethanol was removed by evaporation and the residue was diluted with tert-butyl methyl ether. The mixture was cooled to 0° C. and acidified with 2 N HCl solution. The mixture was allowed to warm to ambient temperature and stirred overnight. The mixture was extracted with DCM. Both organic and aqueous phases contained the product so both they were combined and evaporated. 0.691 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 0.85 (d, 3H), 0.91 (d, 3H), 2.03 (qd, 1H), 4.54 (d, 1H), 6.66 (s, 1H).

Workup

  1. temperatureto warm to RT
  2. temperatureThe solution was heated to 60° C. for 3 h
  3. customEthanol was removed by evaporation
  4. additionthe residue was diluted with tert-butyl methyl ether
  5. temperatureThe mixture was cooled to 0° C.
  6. temperatureto warm to ambient temperature
  7. extractionThe mixture was extracted with DCM
  8. customevaporated

Sources & evidence

ORD record
ord-00520ab2f0214c738fcb209c124ce606
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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