Dimethyl Sulfoxide → HCID 53913346, compound

HRID 862500Notes

Reaction equation

HRID 862500 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][OH:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].CS(C)=O.[CH2:26]1[O:34][CH:27]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(OCC)C>[C:28]1([CH:27]([OH:34])[CH2:26][O:15][CH2:14][CH:10]2[O:11][CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7276Styrene OxideHCID 2776358(4-Benzylmorpholin-2-yl)methanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 53913346HCID 53913346, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4.30 g of 4-benzyl-2-hydroxymethylmorpholine, 930 mg of potassium tert-butoxide and 4 ml of dimethyl sulfoxide was heated to 80° C. Thereto was dropwise added 2.50 g of styrene oxide over 20 minutes. The resulting mixture was stirred for 2 hours at the same temperature. The reaction mixture was added to a mixture of 30 ml of diethyl ether and 30 ml of ice water. The organic layer was separated and mixed with 10 ml of water. The mixture was adjusted to pH 2.0 with 6N hydrochloric acid. The aqueous layer was separated and mixed with 30 ml of diethyl ether. The mixture was adjusted to pH 11 with a 2N aqueous sodium hydroxide solution. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: toluene/ethyl acetate=1/1) to obtain 2.00 g of oily 1-phenyl-2-[(4-benzylmorpholin-2-yl)methoxy]ethanol (compound No. 144).

Workup

  1. customover 20 minutes
  2. customThe organic layer was separated
  3. additionmixed with 10 ml of water
  4. customThe aqueous layer was separated
  5. additionmixed with 30 ml of diethyl ether
  6. customThe organic layer was separated
  7. washwashed with a saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was removed by distillation under reduced pressure
  10. customThe residue was purified by column chromatography (eluant: toluene/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-e053369a804a43ec9e839824d4280191
Source dataset
uspto-grants-1998_02
Patent number
US05719150

Reaction notes

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