Ethyl Acetate → HCID 59253240, compound

HRID 386897Notes

Reaction equation

HRID 386897 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:12][OH:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[H-].[Na+].[CH3:16][O:17][CH2:18][CH2:19]Br.C(OCC)(=O)C>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1([CH2:12][O:13][CH2:19][CH2:18][O:17][CH3:16])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 46172882Ethyl 1-(hydroxymethyl)cyclohexane-1-carboxylate

Product 1

HCID 59253240HCID 59253240, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Hydroxymethyl-cyclohexanecarboxylic acid ethyl ester (2.0 g, 10.9 mmol) is added to a solution of 60% sodium hydride (0.86 g, 21.7 mmol) in 5.0 mL of DMF at 0° C. and the reaction mixture is stirred for 30 minutes; 2-bromoethyl methyl ether (3.0 g, 21.7 mmol) is added over a period of 10 minutes and then the reaction mixture is stirred at room temperature for 14 h. Ice water and 20% ethyl acetate in petroleum ether are added. The two phases are separated and the organic layer is washed with water and brine and dried over Na2SO4. After filtration the solvent is removed under reduced pressure to provide 2.0 g of the title compound as a yellow liquid that is used in the next step without further purification. m/z 245 [M+H].

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 14 h
  2. customThe two phases are separated
  3. washthe organic layer is washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration the solvent
  6. customis removed under reduced pressure

Sources & evidence

ORD record
ord-19cc768ede46475289e766df7f99f15e
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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