Bromide ion → Ethyl (2-methylidenecyclohexyl)acetate

HRID 1245410Notes

Reaction equation

HRID 1245410 reaction equation
[Br-].[H-].[Na+].[CH2:4]([O:6][C:7](=[O:16])[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=O)[CH3:5].[CH3:17]N(C=O)C>>[CH2:4]([O:6][C:7](=[O:16])[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=[CH2:17])[CH3:5]

Participants

5

Reactant 4

HCID 259Bromide ionHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 91229Ethyl 2-oxocyclohexylacetate

Product 1

HCID 12679490Ethyl (2-methylidenecyclohexyl)acetateYield 50%

Conditions

Temperature
0 °C

Procedure

Triphenylphosphoniummethyl bromide (6.9 g, 19.5 mmol) was added to a suspension of sodium hydride (0.78 g, 60% oil dispersion, 19.5 mmol) (hexane washed) in DMF (50 mL) cooled to 0° C. under a nitrogen atmosphere. The reaction was stirred for 1 h, and then (2-oxo-cyclohexyl)-acetic acid ethyl ester (3.0 g, 16.2 mmol) was added. The reaction was allowed to warm to room temperature and stirred for 18 h. The reaction was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give a residue. The product was purified by FCC on silica gel eluting with hexane:ethyl acetate (95:5) to give (2-methylene-cyclohexyl)-acetic acid ethyl ester (1.5 g, 50%) as an oil.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 18 h
  3. customThe reaction was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give a residue
  8. customThe product was purified by FCC on silica gel eluting with hexane:ethyl acetate (95:5)

Sources & evidence

ORD record
ord-110b3519d490411c9150e1774e0cfb28
Source dataset
uspto-grants-2006_10
Patent number
US07125870B2

Reaction notes

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