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

HRID 2259363Notes

Reaction equation

HRID 2259363 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 SulfoxideSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of 6.0g of 2-hydroxymethyl-4-tritylmorpholine, 1.0 g of potassium tert-butoxide and 6 ml of dimethyl sulfoxide was heated to 80° C. Thereto was dropwise added, at 80°-85° C. in 2 hours, a solution 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. additionThereto was dropwise added, at 80°-85° C. in 2 hours
  2. temperatureThe reaction mixture was cooled
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-fc2067e595a64ea9a7ca71099975126f
Source dataset
uspto-grants-1995_12
Patent number
US05472984

Reaction notes

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