Diethyl Ether → HCID 28562150, compound

HRID 1892906Notes

Reaction equation

HRID 1892906 reaction equation
[CH3:1][N:2]([CH3:19])[C:3](=O)[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10](OC)=[O:11])=[CH:8][C:7]=1[O:16][CH3:17].CCOCC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([CH2:10][OH:11])=[CH:8][C:7]=1[O:16][CH3:17]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 16789847HCID 16789847, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 28562150HCID 28562150, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

Methyl 4-{[2-(dimethylamino)-2-oxoethyl]oxy}-3-(methyloxy)benzoate (for a preparation see Intermediate 22) (1.4 g, 5.2 mmol) was dissolved in THF (50 ml) and cooled in an ice-bath under nitrogen. The mixture was then treated cautiously with 1M ether solution of lithium aluminium hydride (5.5 mL) and the mixture was stirred at 5° C. allowing to warm to RT overnight. The reaction mixture was quenched by cautious addition of aq. saturated NaHCO3 solution (1 mL), followed by MgSO4 (2 g) and stirring for 30 min. The solids were removed by filtration, washed with ethyl acetate, and the filtrate was evaporated to give the title compound (1.18 g, 100%) as a yellow oil: LCMS (System A) RT=0.34 min, ES+ve m/z 226 (M+H)+.

Workup

  1. temperaturecooled in an ice-bath under nitrogen
  2. temperatureto warm to RT overnight
  3. customThe reaction mixture was quenched by cautious addition of aq. saturated NaHCO3 solution (1 mL)
  4. stirringstirring for 30 min
  5. customThe solids were removed by filtration
  6. washwashed with ethyl acetate
  7. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-314d0c9af1524aed9b7d371c840d428d
Source dataset
uspto-grants-2013_08
Patent number
US08507543B2

Reaction notes

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