1-Iodopropane → Ethyl 1-propylcyclobutane-1-carboxylate

HRID 2080902Notes

Reaction equation

HRID 2080902 reaction equation
[CH:1]1([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:4][CH2:3][CH2:2]1.[CH:10]([N-]C(C)C)([CH3:12])[CH3:11].[Li+].ICCC>C1COCC1.CS(C)=O>[CH2:8]([O:7][C:5]([C:1]1([CH2:11][CH2:10][CH3:12])[CH2:4][CH2:3][CH2:2]1)=[O:6])[CH3:9]

Participants

6

Reactant 3

HCID 336431-IodopropaneHCID 84700Ethyl cyclobutanecarboxylateHCID 2724682Lithium diisopropylamide

Product 1

HCID 14301362Ethyl 1-propylcyclobutane-1-carboxylateYield 48%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl cyclobutanecarboxylate 1 (25.0 g, 0.195 mol) was added to a solution of lithium diisopropylamide (97.5 mL of a 2.0M solution in THF, 0.195 mol) in THF (200 mL) at −78° C. After 30 min the reaction solution was warmed to room temperature and transferred via cannula to a solution of 1-iodopropane (49.7 g, 0.293 mol) in DMSO (104 mL) while maintaining the temperature between 15-20° C. After stirring for an additional 30 min the precipitated salts were removed by vacuum filtration. The filtrate was concentrated in vacuo, diluted with hexane and washed with 1 N HCl, saturated aqueous NaHCO3 and brine. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by vacuum distillation (105-108° C., 20-30 mmHg) to give 16 g (48%) of the ester 2 as a clear, colorless oil.

Workup

  1. temperaturewhile maintaining the temperature between 15-20° C
  2. customwere removed by vacuum filtration
  3. concentrationThe filtrate was concentrated in vacuo
  4. additiondiluted with hexane
  5. washwashed with 1 N HCl, saturated aqueous NaHCO3 and brine
  6. dry with materialThe organic portion was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. distillationThe residue was purified by vacuum distillation (105-108° C., 20-30 mmHg)

Sources & evidence

ORD record
ord-15761b5f99644c2b93179d2e0498786c
Source dataset
uspto-grants-2011_04
Patent number
US07932420B2

Reaction notes

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