Aluminium lithium hydride → HCID 5064160, compound

HRID 623212Notes

Reaction equation

HRID 623212 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:14](OCC)=[O:15])=[C:11]([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]([CH2:14][OH:15])=[C:11]([CH3:13])[N:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21290688HCID 21290688, compound

Product 1

HCID 5064160HCID 5064160, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

9.3 g (35.1 mmol) of ethyl 2-(4-chlorophenyl)-4-methyl-5-oxazolecarboxylate were dissolved in 40 ml of dry tetrahydrofuran and the solution was added dropwise during 10 minutes to a stirred suspension of 1.75 g (46.1 mmol) of lithium aluminium hydride in 60 ml of dry tetrahydrofuran at 0° C. The suspension was stirred at 0° C. for 1 hour and then at room temperature for 1.5 hours. Excess lithium aluminium hydride was destroyed by the dropwise addition of saturated aqueous sodium sulphate, followed by the addition of 100 ml of dilute aqueous sulphuric acid. The aqueous phase was extracted twice with dichloromethane. The combined extracts were washed once with water, dried over magnesium sulphate, filtered and evaporated. The residue was recrystallized from chloroform/hexane to give 6.44 g (82%) of 2-(4-chlorophenyl)-4-methyl-5-oxazolemethanol of melting point 135° C.

Workup

  1. waitat room temperature for 1.5 hours
  2. customExcess lithium aluminium hydride was destroyed by the dropwise addition of saturated aqueous sodium sulphate
  3. additionfollowed by the addition of 100 ml of dilute aqueous sulphuric acid
  4. extractionThe aqueous phase was extracted twice with dichloromethane
  5. washThe combined extracts were washed once with water
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was recrystallized from chloroform/hexane

Sources & evidence

ORD record
ord-8b4126e7551e40eaad3bc1c4a15229b1
Source dataset
uspto-grants-1988_09
Patent number
US04774253

Reaction notes

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