Lithium Hydroxide → HCID 66739640, compound

HRID 1402747Notes

Reaction equation

HRID 1402747 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:6][O:5][C:4]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][CH:8]=2)=[N:3]1.[Li+].[OH-]>C1COCC1.O.CCOC(C)=O>[CH3:1][C:2]1([CH3:17])[CH2:6][O:5][C:4]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=2)=[N:3]1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 403394HCID 403394, compound

Product 1

HCID 66739640HCID 66739640, compoundYield 16.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 4-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)benzoate (78 mg, 0.33 mmol) in THF (1 mL) and H2O (1 mL) was added LiOH (23 mg, 1 mmol). The mixture was stirred at RT for 4 h before it was diluted with EtOAc (5 mL) and quenched by addition of aqueous HCl (5 ml of a 0.5 M aqueous solution, 2.5 mmol). After extraction with EtOAc (3×10 mL), the combined organic extracts were washed with brine (10 mL), dried (MgSO4), filtered and concentrated at reduced pressure. The crude residue (12 mg, 16% yield) was obtained as colourless oil and was used without further purification.

Workup

  1. customquenched by addition of aqueous HCl (5 ml of a 0.5 M aqueous solution, 2.5 mmol)
  2. extractionAfter extraction with EtOAc (3×10 mL)
  3. washthe combined organic extracts were washed with brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-0508ac74cf014005af19712ff8850deb
Source dataset
uspto-grants-2014_12
Patent number
US08912176B2

Reaction notes

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