Methyl cyclohexanecarboxylate → HCID 86681305, compound

HRID 1430244Notes

Reaction equation

HRID 1430244 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][CH2:22][O:23][CH3:24]>O1CCCC1>[CH3:24][O:23][CH2:22][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 5245511-Bromo-3-methoxypropaneHCID 2724682Lithium diisopropylamide

Product 1

HCID 86681305HCID 86681305, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a cooled (−78° C.) solution of lithium diisopropylamide (2.0 M, 12 mL) in tetrahydrofuran (10 mL) was added methyl cyclohexanecarboxylate (1.42 g) in tetrahydrofuran (10 mL). The mixture was stirred at −78° C. for 30 minutes and a solution of 1-bromo-3-methoxypropane (1.73 g) in tetrahydrofuran (10 mL) was added to the mixture. 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 the solvent gave the 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 the solvent

Sources & evidence

ORD record
ord-c087cc5c744246b3bae5fbbf805bd4cf
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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