Sodium Hydroxide → 2-Chloro-6-morpholinopyran-4-one

HRID 33780Notes

Reaction equation

HRID 33780 reaction equation
[Cl:1][C:2](Cl)=[CH:3][C:4](=[O:14])[CH2:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[O:7].Cl(O)(=O)(=O)=O.[OH-].[Na+]>O1CCOCC1>[Cl:1][C:2]1[O:7][C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:5][C:4](=[O:14])[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24247Perchloric AcidHCID 66052615,5-Dichloro-1-morpholinopent-4-ene-1,3-dione

Product 1

HCID 66052622-Chloro-6-morpholinopyran-4-oneYield 75.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 2 (11.3 g, 44.9 mmol) in dioxane was added perchloric acid (11.4 ml, 0.14 mol) and the reaction was heated at 90° C. under N2 for 1 hour. The reaction was cooled, neutralised with 2M NaOH (75 ml) and filtered. The aqueous layer was extracted with DCM (4×30 ml) and the organic layers were combined and dried over MgSO4. The organic layer was further treated with charcoal and filtered through celite. The dark yellow filtrate was evaporated in vacuo, and the resulting solid was triturated with hexane (50 ml) and dried to give 3 (7.3 g, 75%) as a light yellow powder. m/z (LC-MS, ESP): 216 (M++1). 1H-NMR (300 MHz, DMSO-d6): 3.3 (t, 4H), 3.65 (t, 4H), 5.4 (d, 1H), 6.25 (d, 1H).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. extractionThe aqueous layer was extracted with DCM (4×30 ml)
  4. dry with materialdried over MgSO4
  5. additionThe organic layer was further treated with charcoal
  6. filtrationfiltered through celite
  7. customThe dark yellow filtrate was evaporated in vacuo
  8. customthe resulting solid was triturated with hexane (50 ml)
  9. customdried

Sources & evidence

ORD record
ord-39173e7f8abd44aa9174da35c16bc802
Source dataset
uspto-grants-2008_09
Patent number
US07429660B2

Reaction notes

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