Diethyl Ether → HCID 57426006, compound

HRID 2216528Notes

Reaction equation

HRID 2216528 reaction equation
[CH3:1][C:2]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)=[O:3].[H-].[Na+].[C:12](OCC)(=[O:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14].CCOCC>CN(C=O)C>[CH:4]1([C:2](=[O:3])/[CH:1]=[C:12](\[OH:18])/[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7268Diethyl OxalateHCID 13207Cyclohexyl methyl ketoneHCID 24758Sodium hydride

Product 1

HCID 57426006HCID 57426006, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of cyclohexyl methyl ketone (10.4 g, 82.4 mmol) in DMF (90 ml) at rt, was added 60% NaH (3.96 g, 98.9 mmol). The mixture was stirred 45 min, cooled to 0° C., diethyl oxalate (13.4 ml, 98.9 mmol) was added and the temperature allowed to warm and stay at rt for 3 h. The reaction mixture was poured into Et2O, extracted with H2O (3×), and the aqueous phase was acidified with conc. HCl and extracted with EtOAc (3×). The organic extracts were washed with brine, dried (Na2SO4), and concentrated to afford 17.45 g (94%) of 9.1. MS (ESI) 225.2 (MH+).

Workup

  1. temperatureto warm
  2. waitstay at rt for 3 h
  3. extractionextracted with H2O (3×)
  4. extractionextracted with EtOAc (3×)
  5. washThe organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f42de545eaa24e0381105e624e3f15b3
Source dataset
uspto-grants-2006_09
Patent number
US07112601B2

Reaction notes

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