1,4-Dibromobutane → HCID 58525273, compound

HRID 2191589Notes

Reaction equation

HRID 2191589 reaction equation
[CH:1]1([C:4](=[O:10])[CH2:5][C:6]([O:8][CH3:9])=[O:7])[CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:14][CH2:15][CH2:16][CH2:17]Br>CN(C=O)C>[CH3:9][O:8][C:6]([C:5]1([C:4]([CH:1]2[CH2:3][CH2:2]2)=[O:10])[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:7]

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 101300163-Cyclopropyl-3-Oxopropionic Acid Methyl Ester

Product 1

HCID 58525273HCID 58525273, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-cyclopropyl-3-oxopropanoate (2.0 g, 14 mmol) in DMF (70 mL) was added sodium hydride (60% in mineral oil, 1.41 g, 35 mmol). The reaction mixture was stirred for 10 min then 1,4-dibromobutane (1.85 mL, 15 mmol) was slowly added. The reaction mixture was stirred for 2.5 h then carefully quenched with water and extracted with diethyl ether (2×). The combined organics were washed with water (2×) and brine then dried over Na2SO4 and concentrated. The residue was purified by chromatography over 60 g SiO2 (0% to 10% EtOAc/hexanes) to afford 0.63 g (23%) of 1-cyclopropanecarbonyl-cyclopentane carboxylic acid methyl ester as a colorless oil.

Workup

  1. stirringThe reaction mixture was stirred for 2.5 h
  2. customthen carefully quenched with water
  3. extractionextracted with diethyl ether (2×)
  4. washThe combined organics were washed with water (2×) and brine
  5. dry with materialthen dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography over 60 g SiO2 (0% to 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-269a37e829a645bca8bb1590eeb73949
Source dataset
uspto-grants-2012_12
Patent number
US08329699B2

Reaction notes

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