Sodium sulfate decahydrate → HCID 21474717, compound

HRID 1901758Notes

Reaction equation

HRID 1901758 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][CH2:6][CH:7]1[CH2:12][N:11]([CH:13]([CH3:19])[C:14](OCC)=[O:15])[C:10](=O)[CH2:9][O:8]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][CH2:6][CH:7]1[CH2:12][N:11]([CH:13]([CH3:19])[CH2:14][OH:15])[CH2:10][CH2:9][O:8]1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydride2×HCID 21474707HCID 21474707, compound

Product 1

HCID 21474717HCID 21474717, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.50 g of ethyl 2-[6-(3-chlorophenoxymethyl)-3-oxomorpholin-4-yl]propionate in 10 ml of anhydrous tetrahydrofuran was added dropwise to a suspension of 0.51 g of lithium aluminum hydride in 20 ml of anhydrous tetrahydrofuran, whilst ice-cooling. The mixture was stirred at room temperature for 2.5 hours, after which excess lithium aluminum hydride was decomposed by adding sodium sulfate decahydrate to the mixture. Insolubles were then removed from the reaction mixture by filtration with the help of a Celite (trade name) filter aid, and the solvent was removed from the filtrate by evaporation under reduced pressure, to give 0.97 g of the title compound having an Rf value of 0.19 (on silica gel thin layer chromatography, using a 3:1 by volume mixture of ethyl acetate and hexane as the developing solvent).

Workup

  1. temperaturecooling
  2. customInsolubles were then removed from the reaction mixture by filtration with the help of a Celite (trade name)
  3. filtrationfilter aid
  4. customthe solvent was removed from the filtrate by evaporation under reduced pressure

Sources & evidence

ORD record
ord-e215c7fad4f3495da96b90ff62b101c0
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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