Pyridine → 1-(Acetyloxy)cyclopropane-1-carboxylic acid
Reaction equation
[OH:1][C:2]1([C:5]([OH:7])=[O:6])[CH2:4][CH2:3]1.N1C=CC=CC=1.[C:14](Cl)(=[O:16])[CH3:15]>C(Cl)Cl>[C:14]([O:1][C:2]1([C:5]([OH:7])=[O:6])[CH2:4][CH2:3]1)(=[O:16])[CH3:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1-hydroxy-cyclopropanecarboxylic acid (100 mg, 0.98 mmol) and pyridine (100 μL) in 3 mL of DCM is cooled to 0° C. A solution of acetyl chloride (80 μL, 1.18 mmol) in 3 mL of DCM is then added dropwise to the ice cold mixture. After the addition, the resulting mixture is stirred at room temperature for 3 h. Next, the mixture is washed with saturated NH4Cl. The aqueous phase is extracted twice with DCM. The combined organic phases are combined, dried over MgSO4, filtered, and evaporated to afford the desired product that is used as such.
Workup
- additionAfter the addition
- washNext, the mixture is washed with saturated NH4Cl
- extractionThe aqueous phase is extracted twice with DCM
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-64b511306f1943cf9783a0a11513fc53
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09351955B2
Reaction notes
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