Lithium hydroxide, monohydrate → HCID 82125097, compound

HRID 82210Notes

Reaction equation

HRID 82210 reaction equation
O.[OH-].[Li+].[CH:4]1([C:7]2[O:8][CH:9]=[C:10]([CH2:12][C:13]([O:15]CC)=[O:14])[N:11]=2)[CH2:6][CH2:5]1>C1COCC1.O>[CH:4]1([C:7]2[O:8][CH:9]=[C:10]([CH2:12][C:13]([OH:15])=[O:14])[N:11]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86672106Ethyl 2-(2-cyclopropyloxazol-4-yl)acetate

Product 1

HCID 82125097HCID 82125097, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (7.83 g, 186.7 mmol) was added to ethyl (2-cyclopropyl-1,3-oxazol-4-yl)acetate (Preparation 154, 7.00 g, 35.9 mmol) in THF (200 mL) and water (100 mL). The mixture was stirred at room temperature for 2 hours then the reaction mixture volume was reduced to one third by evaporation in vacuo. The aqueous residue was acidified using aqueous HCl (1.0 M) then extracted with EtOAc (200 mL). The organic phase was evaporated in vacuo and the crude material was triturated with diethyl ether (100 mL) to afford the title compound as a white solid in 66% yield, 4.00 g.

Workup

  1. customthe reaction mixture volume was reduced to one third by evaporation in vacuo
  2. extractionthen extracted with EtOAc (200 mL)
  3. customThe organic phase was evaporated in vacuo
  4. customthe crude material was triturated with diethyl ether (100 mL)

Sources & evidence

ORD record
ord-99f63dc072ae404fa418fbbaec48ec6b
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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