Sodium Carbonate → HCID 58230019, compound

HRID 2092702Notes

Reaction equation

HRID 2092702 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9](=[CH2:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[Li+].CC([N-]C(C)C)C.[CH3:21][O:22][CH2:23][CH2:24]Br.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.O>[CH2:1]([O:3][C:4]([C:6]1([CH2:24][CH2:23][O:22][CH3:21])[CH2:11][CH2:10][C:9](=[CH2:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 809722-Bromoethyl methyl etherHCID 2724682Lithium diisopropylamideHCID 15151435Ethyl 4-methylidenecyclohexane-1-carboxylate

Product 1

HCID 58230019HCID 58230019, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 5 g (30 mmol) 4-methylene-cyclohexanecarboxylic acid ethyl ester (commercially available) in 19 mL THF was added to 59 mmol LDA in 75 mL THF at −5° C. and stirred for 3 h. 8.2 g (59 mmol) 2-bromoethyl methyl ether in 10 mL THF was added and the mixture was allowed to stir to room temperature and stirred additionally over night. Water and 2M Na2CO3 aq. was added and the mixture was evaporated to dryness. The residue was taken up in ethyl acetate washed with water and brine, dried with MgSO4, filtered and evaporated. The residue was purified by flash column chromatography over silica eluting with a gradient formed from hexane and ethyl acetate to yield after evaporation of the product containing fractions 4.98 g (74%) of the title compound as yellow liquid.

Workup

  1. stirringto stir to room temperature
  2. stirringstirred additionally over night
  3. customthe mixture was evaporated to dryness
  4. washwashed with water and brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash column chromatography over silica eluting with a gradient
  9. customformed from hexane and ethyl acetate
  10. customto yield
  11. customafter evaporation of the product
  12. additioncontaining fractions 4.98 g (74%) of the title compound as yellow liquid

Sources & evidence

ORD record
ord-6a8c3f97d36541f1ac941004f1c8d596
Source dataset
uspto-grants-2013_05
Patent number
US08440710B2

Reaction notes

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