Lithium Hydroxide → 1-(Pyridazin-3-yl)cyclopropane-1-carboxylic acid

HRID 931174Notes

Reaction equation

HRID 931174 reaction equation
[OH-].[Li+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2([C:12]([O:14]CC)=[O:13])[CH2:11][CH2:10]2)[N:4]=1>O1CCCC1.O>[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2([C:12]([OH:14])=[O:13])[CH2:10][CH2:11]2)[N:4]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 89853348Ethyl 1-(pyridazin-3-yl)cyclopropanecarboxylate

Product 1

HCID 717777681-(Pyridazin-3-yl)cyclopropane-1-carboxylic acidYield 0.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (196.4 mg, 4.68 mmol) was added to a solution of ethyl 1-(pyridazin-3-yl)cyclopropanecarboxylate (300 mg, 156 mmol) in tetrahydrofuran and water (1:1, 10 mL) at room temperature. The reaction mixture was stirred for 2 h and concentrated. The resulting residue was dissolved in water and the pH was adjusted to 2 using 1N aqueous hydrochloric acid. The mixture was extracted with ethyl acetate. The organics were dried over sodium sulfate and concentrated to afford the title compound (160 mg) which was used as is without further purification. MS (ES+APCI) (M−H) 163.0; LCMS retention time: 2.713 minutes (Method X1)

Workup

  1. concentrationconcentrated
  2. dissolutionThe resulting residue was dissolved in water
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialThe organics were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-14769412112f4cb49dcabaeb1e229529
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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