Dimethyl Ether → 2-(2,6-Dimethylmorpholin-4-yl)ethan-1-ol

HRID 2255373Notes

Reaction equation

HRID 2255373 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].COC.[CH3:10][CH:11]1[O:16][CH:15]([CH3:17])[CH2:14][N:13]([CH2:18][C:19](OCC)=[O:20])[CH2:12]1>>[OH:20][CH2:19][CH2:18][N:13]1[CH2:14][CH:15]([CH3:17])[O:16][CH:11]([CH3:10])[CH2:12]1

Participants

4

Reactant 3

HCID 8254Dimethyl EtherHCID 13191864HCID 13191864, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 3407042-(2,6-Dimethylmorpholin-4-yl)ethan-1-olYield 67%

Conditions

Temperature
0 °C

Procedure

To a flask was added 22.8 g. (0.6 mole) of lithium aluminum hydride in 300 ml. of dimethyl ether. The stirred slurry was cooled to 0° C. and then 26.5 g. (0.15 mole) of ethyl 2,6-dimethyl-4-morpholinylacetate was slowly added. The reaction was allowed to warm to room temperature and stirred for 18 hours. It was then quenched with aqueous ammonium chloride, filtered, and extracted with diethyl ether. The solvent was concentrated to give 15.5 g. (67% yield) of the desired intermediate.

Workup

  1. additionTo a flask was added 22.8 g
  2. temperatureto warm to room temperature
  3. customIt was then quenched with aqueous ammonium chloride
  4. filtrationfiltered
  5. extractionextracted with diethyl ether
  6. concentrationThe solvent was concentrated
  7. customto give 15.5 g

Sources & evidence

ORD record
ord-d356632dd57740eaba9f69a8aab168e0
Source dataset
uspto-grants-1993_08
Patent number
US05240925

Reaction notes

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