2,3-Dichloropropene → HCID 86665069, compound

HRID 333344Notes

Reaction equation

HRID 333344 reaction equation
[CH:1]1([C:6]([O:8][CH3:9])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].CC([N-]C(C)C)C.[Cl:18][C:19]([CH2:21]Cl)=[CH2:20]>C1COCC1>[Cl:18][C:19](=[CH2:20])[CH2:21][C:1]1([C:6]([O:8][CH3:9])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 65652,3-DichloropropeneHCID 78365Methyl cyclopentanecarboxylateHCID 2724682Lithium diisopropylamide

Product 1

HCID 86665069HCID 86665069, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of methyl cyclopentanecarboxylate (2.0 g, 15.60 mmol) in THF (70 mL) cooled to −78° C. was added 2 M solution of LDA in THF (10.1 mL, 20.3 mmol). The mixture was stirred at −78° C. for 1 hour. To this mixture was added 2,3-dichloroprop-1-ene (3.46 g, 31.2 mmol) and allowed to warm to room temperature. The reaction mixture was quenched with aq. NH4Cl and extracted with EtOAc. The organic layer was washed with water, brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The obtained residue was purified by chromatography using EtOAc/heptane gradient to give methyl 1-(2 chloroallyl)cyclopentanecarboxylate (1.82 g). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.46-1.75 (m, 6H), 1.98-2.18 (m, 2H), 2.66 (s, 2H), 3.61 (s, 3H), 5.02 (d, J=1.3 Hz, 1H), 5.14 (d, J=1.3 Hz, 1H).

Workup

  1. temperatureto warm to room temperature
  2. customThe reaction mixture was quenched with aq. NH4Cl
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by chromatography

Sources & evidence

ORD record
ord-fd5eaf636ab34fb1837e3944a64aaafa
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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