Water → (E)-4-morpholino-2-buten-1-ol

HRID 2288206Notes

Reaction equation

HRID 2288206 reaction equation
[H-].COCCO[Al+]OCCOC.[Na+].[H-].[O:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]#[C:23][CH2:24][OH:25])[CH2:17][CH2:16]1.O.[OH-].[Na+]>C1(C)C=CC=CC=1.O1CCCC1>[O:15]1[CH2:20][CH2:19][N:18]([CH2:21]/[CH:22]=[CH:23]/[CH2:24][OH:25])[CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 31128494-Morpholinobut-2-YN-1-OLHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 22478312(E)-4-morpholino-2-buten-1-olYield 35.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
4.5 °C

Procedure

Tetrahydrofuran (15 ml) was added to 70% solution of sodium bis(2-methoxyethoxy)aluminum hydride in toluene (49.7 g) under an atmosphere of nitrogen and then cooled. A solution of 4-morpholino-2-butyn-1-ol (3.0 g) in tetrahydrofuran (15 ml) was added dropwise maintaining the reaction temperature 4-5° C. After being stirred for 10 minutes, the reaction mixture was allowed to warm room temperature. After 1 hour, water (6 ml) and 10% aqueous sodium hydroxide solution (4.5 ml) were added cautiously and then filtered. The filtrate was dried over potassium carbonate and concentrated under reduced pressure to give an oily product, which was purified by column chromatography on silica gel using ethyl acetate-methanol (5:1) to afford (E)-4-morpholino-2-buten-1-ol (1.08 g).

Workup

  1. temperaturecooled
  2. temperatureto warm room temperature
  3. waitAfter 1 hour
  4. filtrationfiltered
  5. dry with materialThe filtrate was dried over potassium carbonate
  6. concentrationconcentrated under reduced pressure
  7. customto give an oily product, which
  8. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c02824728a0849a6abedd6c1f8dfde3d
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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