Sodium Hydroxide → 1-(3-(Hydroxymethyl)isoxazol-5-yl)ethanone

HRID 416276Notes

Reaction equation

HRID 416276 reaction equation
[CH3:1][C:2]1([C:7]2[O:11][N:10]=[C:9]([CH2:12][OH:13])[CH:8]=2)OCC[O:3]1.[OH-].[Na+]>CO>[OH:13][CH2:12][C:9]1[CH:8]=[C:7]([C:2](=[O:3])[CH3:1])[O:11][N:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58930623(5-(2-Methyl-1,3-dioxolan-2-yl)isoxazol-3-yl)methanol

Product 1

HCID 589304951-(3-(Hydroxymethyl)isoxazol-5-yl)ethanoneYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of the carbinol 319 (2.39 g, 12.9 mmol) in MeOH (30 mL) 10% HCl (30 mL) was added. The reaction mixture was stirred at 70° C. for 18 hours, cooled and neutralized to pH 6 using 1M NaOH solution. MeOH was evaporated and the resulting aqueous phase was extracted with EtOAc. The organic layer was washed with brine, dried under MgSO4 and concentrated under reduced pressure to produce the title compound as a beige solid (1.67 g, 92% yield), which was used for next step without further purification. 1H NMR (DMSO-d6) δ (ppm): 7.25 (s, 1H), 5.62 (t, J=6.1 Hz, 1H), 4.56 (d, J=5.9 Hz, 2H), 2.56 (s, 3H). MS (m/z): 141.12 (calc) 142.1 (MH+) (found)

Workup

  1. temperaturecooled and neutralized to pH 6
  2. customMeOH was evaporated
  3. extractionthe resulting aqueous phase was extracted with EtOAc
  4. washThe organic layer was washed with brine
  5. customdried under MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-13188c699154478db703bb4a70f45bd8
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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