Water → HCID 23458393, compound

HRID 1679989Notes

Reaction equation

HRID 1679989 reaction equation
[OH:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[O:4][CH:5]([CH:12]1[O:17][CH2:16][C:15](=[O:18])[N:14]([CH3:19])[CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][CH3:32].O>CN(C=O)C>[CH2:31]([O:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[O:4][CH:5]([CH:12]1[O:17][CH2:16][C:15](=[O:18])[N:14]([CH3:19])[CH2:13]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 23458286HCID 23458286, compound

Product 1

HCID 23458393HCID 23458393, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 10 g of 2-[α-(2-hydroxy-phenoxy)-benzyl]-4-methylmorpholin -5-one in 150 ml of anhydrous DMF addition was made of 4.8 g of potassium carbonate, and then dropwise addition was made under stirring of 2.6 ml of bromoethane in 20 ml of DMF. The mixture was heated for 4 hours at 60° C. under stirring. The mixture was poured into 1.5 liters of water and extracted with ethyl acetate. The organic extracts were washed with H2O, dehydrated over Na2SO4 and concentrated under reduced pressure. There was obtained 8.49 g (Yield 78%) of 2-[α-(2-ethoxy-phenoxy)-benzyl]-4-methyl-morpholin -5-one.

Workup

  1. additiondropwise addition
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with H2O
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a0bb2325dd254ba08c89479782a9d243
Source dataset
uspto-grants-1981_06
Patent number
US04271160

Reaction notes

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