Lithium hydroxide, monohydrate → HCID 59129198, compound

HRID 1403872Notes

Reaction equation

HRID 1403872 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([C:11]3([C:14]([O:16]C)=[O:15])[CH2:13][CH2:12]3)[CH:9]=[CH:10][C:5]=2[O:4][N:3]=1.O[Li].O>CO.O>[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([C:11]3([C:14]([OH:16])=[O:15])[CH2:12][CH2:13]3)[CH:9]=[CH:10][C:5]=2[O:4][N:3]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59129328HCID 59129328, compound

Product 1

HCID 59129198HCID 59129198, compoundYield 32.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of methyl 1-(3-methylbenzo[d]isoxazol-5-yl)cyclopropanecarboxylate (1.5 g, 6.5 mmol) in MeOH (20 mL) and water (2 mL) was added LiOH.H2O (0.80 g, 19 mmol) in portions at room temperature. The reaction mixture was stirred at room temperature overnight before the MeOH was removed by evaporation under vacuum. Water and Et2O were added and the aqueous layer was separated, acidified with HCl and extracted with EtOAc (50 mL×3). The combined organic extracts were dried over anhydrous Na2SO4 and evaporated under vacuum to give 1-(3-methylbenzo[d]isoxazol-5-yl)cyclopropanecarboxylic acid (455 mg, 32%). 1H NMR (400 MHz, DMSO) δ 12.40 (br s, 1H), 7.76 (s, 1H), 7.60-7.57 (m, 2H), 2.63 (s, 3H), 1.52-1.48 (m, 2H), 1.23-1.19 (m, 2H). MS (ESI) m/z (M+H+) 218.1.

Workup

  1. customwas removed by evaporation under vacuum
  2. additionWater and Et2O were added
  3. customthe aqueous layer was separated
  4. extractionextracted with EtOAc (50 mL×3)
  5. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-2ed53eebd3f54eabb7374473470a8498
Source dataset
uspto-grants-2014_12
Patent number
US08912199B2

Reaction notes

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