Potassium Hydroxide → HCID 19430222, compound

HRID 854651Notes

Reaction equation

HRID 854651 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[N:10][C:9]=1[C:20](OCC)=[O:21].[O-]S([O-])(=O)=O.[Mg+2].[OH-].[K+]>C(OCC)C.C(OCC)(=O)C.C(OC)(C)(C)C.CCCCCCC.C(OCC)(=O)C>[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[N:10][C:9]=1[CH2:20][OH:21]

Participants

9

Reactant 4

HCID 14797Potassium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 58934123HCID 58934123, compound

Product 1

HCID 19430222HCID 19430222, compoundYield 96.5%

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolventHCID 15413tert-Butyl methyl etherSolventHCID 21899848Ethylacetate heptaneSolvent

Conditions

Temperature
0 °C

Procedure

In a dry four-necked flask with stirrer motor, internal thermometer, dropping funnel with pressure equalizer and reflux condenser with argon inlet (aspirator with tap), 9.3 g of LiAlH4 are covered with 600 ml of diethyl ether. The suspension is cooled to 0° C. 30 g of ethyl 5-methyl-2-p-tolyloxazole-4-carboxylate are dissolved in 100 ml of diethyl ether and added dropwise to the suspension. After one hour of stirring at room temperature, the reaction has ended (TLC (heptane/ethyl acetate 1:1): Rf, starting material=0.66, Rf, product=0.18). 80 g of MgSO4, 300 ml of methyl tert-butyl ether and 30 ml of ethyl acetate are added successively, and the suspension is stirred at room temperature. The mixture is then cooled to 0° C., 90 ml of 10N KOH are added dropwise and the mixture is stirred for another 60 min. The solids are filtered off, the residue is washed three times with ethyl acetate and the filtrate is concentrated, giving 24 g of 5-methyl-2-p-tolyl-oxazole-4-methanol as a yellow solid. C12H13NO2 (203.24), LCMS(ESI): 204.1 (MH+).

Workup

  1. customIn a dry four-necked flask with stirrer motor, internal thermometer, dropping
  2. additionadded dropwise to the suspension
  3. stirringthe suspension is stirred at room temperature
  4. temperatureThe mixture is then cooled to 0° C.
  5. stirringthe mixture is stirred for another 60 min
  6. filtrationThe solids are filtered off
  7. washthe residue is washed three times with ethyl acetate
  8. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-a64cc898f46444b49b426ee65e28c948
Source dataset
uspto-grants-2007_08
Patent number
US07259177B2

Reaction notes

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