Cyclopropanecarbonyl chloride → tert-Butyl cyclopropanecarboxylate

HRID 501345Notes

Reaction equation

HRID 501345 reaction equation
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].[CH:7]1([C:10](Cl)=[O:11])[CH2:9][CH2:8]1.C(=O)(O)[O-].[Na+]>CCOCC>[C:2]([O:4][C:10]([CH:7]1[CH2:9][CH2:8]1)=[O:11])([CH3:5])([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 13676038tert-Butyl cyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 12.09 (107.1 mmol) of potassium t-butoxide in 200 mL ether at 0° C. under nitrogen was added 13.4 g (128.6 mmol) of cyclopropanecarboxylic acid chloride over 5 min. After 30 min at 0° C. the mixture was stirred at ambient temperature for an additional 30 min. The reaction mixture was poured into aqueous saturated sodium bicarbonate and extracted with ether. The organic layer was dried and carefully concentrated to deliver 15.0 g (99%) of a yellow oil as the desired ester product.

Workup

  1. extractionextracted with ether
  2. customThe organic layer was dried
  3. concentrationcarefully concentrated

Sources & evidence

ORD record
ord-a1b727301538490faf6608fcdb945a36
Source dataset
uspto-grants-2010_08
Patent number
US07772252B2

Reaction notes

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