Methyl cyclohexanecarboxylate → HCID 86681303, compound

HRID 1430241Notes

Reaction equation

HRID 1430241 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH:9]1([C:15]([O:17][CH3:18])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.Br[CH2:20][CH2:21][O:22][CH3:23]>O1CCCC1>[CH3:23][O:22][CH2:21][CH2:20][C:9]1([C:15]([O:17][CH3:18])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 20748Methyl cyclohexanecarboxylateHCID 809722-Bromoethyl methyl etherHCID 2724682Lithium diisopropylamide

Product 1

HCID 86681303HCID 86681303, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a cooled (−78° C.) solution of lithium diisopropylamide (2.0 M, 20 mL) in tetrahydrofuran (20 mL) was added methyl cyclohexanecarboxylate (5.0 g) in tetrahydrofuran (30 mL). The mixture was stirred at −78° C. for 30 minutes and a solution of 1-bromo-2-methoxyethane (5.86 g) in tetrahydrofuran (10 mL) was added. The mixture was stirred overnight and the temperature was allowed to warm up to room temperature. The mixture was quenched with aqueous NH4Cl and extracted with ethyl acetate (200 mL) and washed with water (3×), brine and dried over Na2SO4. Filtration and evaporation of solvent gave crude product which was used in the next reaction without further purification.

Workup

  1. stirringThe mixture was stirred overnight
  2. temperatureto warm up to room temperature
  3. customThe mixture was quenched with aqueous NH4Cl
  4. extractionextracted with ethyl acetate (200 mL)
  5. washwashed with water (3×), brine
  6. dry with materialdried over Na2SO4
  7. filtrationFiltration and evaporation of solvent
  8. customgave crude product which
  9. customwas used in the next reaction without further purification

Sources & evidence

ORD record
ord-3a60d40f83bc48ccbad956d01d490e81
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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