Cyclopropanecarbonyl chloride → tert-Butyl cyclopropanecarboxylate

HRID 2111757Notes

Reaction equation

HRID 2111757 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 12.0 g (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-873c2b89f48e4ee7a6af8cf435b72baa
Source dataset
uspto-grants-2009_04
Patent number
US07521445B2

Reaction notes

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