Pyridine → 1-(Acetyloxy)cyclopropane-1-carboxylic acid

HRID 529969Notes

Reaction equation

HRID 529969 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

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 27331601-Hydroxy-1-cyclopropanecarboxylic acid

Product 1

HCID 143196251-(Acetyloxy)cyclopropane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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

  1. additionAfter the addition
  2. washNext, the mixture is washed with saturated NH4Cl
  3. extractionThe aqueous phase is extracted twice with DCM
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-64b511306f1943cf9783a0a11513fc53
Source dataset
uspto-grants-2016_05
Patent number
US09351955B2

Reaction notes

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