Water → 1-(Benzo[d]oxazol-2-yl)cyclopropanecarboxylic acid

HRID 2241358Notes

Reaction equation

HRID 2241358 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1([C:13]([O:15]C)=[O:14])[CH2:12][CH2:11]1.C1COCC1.O.[Li+].[OH-]>C(OCC)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1([C:13]([OH:15])=[O:14])[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68518116Methyl 1-(benzo[d]oxazol-2-yl)cyclopropanecarboxylate

Product 1

HCID 685133131-(Benzo[d]oxazol-2-yl)cyclopropanecarboxylic acidYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of methyl 1-(benzo[d]oxazol-2-yl)cyclopropanecarboxylate (0.132 g, 0.6077 mmol) in 3 mL 3:2 THF:H2O at room temperature under nitrogen was added LiOH (0.02911 g, 1.215 mmol). After stirring at ambient temperature overnight the reaction was diluted to 30 mL with ethyl acetate and washed with 2N HCl, water and brine. The organics were dried (MgSO4), filtered and concentrated to a white solid (100 mg, 81% yield).

Workup

  1. washwashed with 2N HCl, water and brine
  2. dry with materialThe organics were dried (MgSO4)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-15b1df92e5eb48e2a9410c3b1482d797
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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