Ethyl Acetate → 1(2-Naphthyl)-2-[(4-tritylmorpholin-2-yl)methoxy]ethanol

HRID 976521Notes

Reaction equation

HRID 976521 reaction equation
[OH:1][CH2:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4]1.CC(C)([O-])C.[K+].[CH:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][C:35]=1[CH:44]1[CH2:46][O:45]1.C(OCC)(=O)C>CS(C)=O>[CH:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][C:35]=1[CH:44]([OH:45])[CH2:46][O:1][CH2:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:4]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 303332-(Naphthalen-2-yl)oxiraneHCID 23665647Potassium tert-butoxideHCID 544430302-Hydroxymethyl-4-tritylmorpholine

Product 1

HCID 544659661(2-Naphthyl)-2-[(4-tritylmorpholin-2-yl)methoxy]ethanolYield 103.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

a mixture of 6.0 g of 2-hydroxymethyl-4-tritylmorpholine, 1.0 g of potassium tert-butoxide and 6 ml of 2.8 g of 2-(2-naphthyl)oxirane dissolved in 6 ml of dimethyl sulfoxide. The resulting mixture was stirred at the same temperature for 3 hours. The reaction mixture was cooled and added to a mixture of 60 ml of ice water and 60 ml of ethyl acetate. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 9.0 g of oily 1(2-naphthyl)-2-[(4-tritylmorpholin-2-yl)methoxy]ethanol (compound No. 254).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-eaa526f7e658409eb5255db72d1e9e80
Source dataset
uspto-grants-1997_03
Patent number
US05612381

Reaction notes

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