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

HRID 2249569Notes

Reaction equation

HRID 2249569 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 canula 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 1N 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 1N 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-803df178bf4944c3aa864346c40945e8
Source dataset
uspto-grants-2008_01
Patent number
US07314890B2

Reaction notes

Loading…