Dimethylformamide → HCID 90043982, compound

HRID 524659Notes

Reaction equation

HRID 524659 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].CN(C=O)C.[OH-].[Na+].[CH2:19]([N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH:27]1[CH2:32]Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CCOC(C)=O>[CH2:19]([N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH:27]1[CH2:32][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7761Diethyl MalonateHCID 14798Sodium HydroxideHCID 77896150HCID 77896150, compound

Product 1

HCID 90043982HCID 90043982, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Diethyl malonate (1.78 g, 11.1 mmol), DMF (25 mL), sodium hydroxide (0.22 g, 5.55 mmol) and 4-benzyl-3-(bromomethyl)morpholine (1 g, 3.7 mmol) (The compound was synthesized according to the procedure as described in Helvetica Chimica Acta, 87, 2004) were added to a dried flask in turn. The mixture was stirred at 80° C. for 4 hours under N2, and cooled to 25° C. The reaction mixture was diluted with EtOAc (200 mL). The organic layer was washed with brine (100 mL×6), dried over unhydrous Na2SO4. The crude product was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=15/1) to give the title compound as colorless oil (1.15 g, 89%). The compound was characterized by the following spectroscopic data:

Workup

  1. additionwere added to a dried flask in turn
  2. temperaturecooled to 25° C
  3. washThe organic layer was washed with brine (100 mL×6)
  4. dry with materialdried over unhydrous Na2SO4
  5. customThe crude product was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=15/1)

Sources & evidence

ORD record
ord-fb9022739dd441babcf99d9f6e1a92fd
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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