Water → 80875-33-8

HRID 1650082Notes

Reaction equation

HRID 1650082 reaction equation
[CH:1]1([C:5](Cl)=[O:6])[CH2:4][CH2:3][CH2:2]1.[C:8]([Mg]Cl)([CH3:11])([CH3:10])[CH3:9].O>CCOCC>[CH3:9][C:8]([CH3:11])([C:5]([CH:1]1[CH2:4][CH2:3][CH2:2]1)=[O:6])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 78705Cyclobutanecarbonyl chlorideHCID 178418310HCID 178418310, compound

Product 1

HCID 1440585480875-33-8

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-70 °C

Procedure

Cuprous iodide (1.0 gm) was added to a solution of cyclobutane carboxylic acid chloride (15.0 gms) in dry ether (40 mls) under an argon atmosphere. The suspension was stirred and cooled to -70° C. A solution of t-butyl magnesium chloride in ether (61.4 mls of 2M solution) was then added dropwise, whilst the temperature was maintained below -70° C. After the addition was complete, stirring was continued at -70° C. for 1 hour and then for several hours whilst the temperature was allowed to reach 20° C. Water was carefully added to the mixture. The ether layer was separated, combined with an extract of the aqueous phase and washed with dilute caustic soda. Drying and evaporation gave 4.9 gms of yellow oily product. Gas chromatography showed 80% of a major component. The product was used without further purification.

Workup

  1. temperaturewas maintained below -70° C
  2. additionAfter the addition
  3. stirringstirring
  4. waitfor several hours whilst the temperature was allowed
  5. customto reach 20° C
  6. customThe ether layer was separated
  7. extractionan extract of the aqueous phase
  8. washwashed with dilute caustic soda
  9. customDrying
  10. customevaporation

Sources & evidence

ORD record
ord-a8ca19fd13c2466cb3e52437cae769e0
Source dataset
uspto-grants-1990_05
Patent number
US04923502

Reaction notes

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