Iodoethane → 3-(4-Benzyloxyphenyl)-2-ethoxypropanoic acid ethyl ester

HRID 1354887Notes

Reaction equation

HRID 1354887 reaction equation
[OH:1][CH:2]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[OH-].[K+].[CH2:25](I)[CH3:26]>CS(C)=O>[CH2:25]([O:1][CH:2]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:26]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 14797Potassium HydroxideHCID 151861533-(4-Benzyloxyphenyl)-2-hydroxypropionic acid ethyl ester2×

Product 1

HCID 110779683-(4-Benzyloxyphenyl)-2-ethoxypropanoic acid ethyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of racemic ethyl 2-hydroxy-3-(4-benzyloxyphenyl)propionate of the formula (10) (70 g) obtained according to the procedure described in step (iii) above. potassium hydroxide (26 g), dimethylsulphoxide (280 ml) and molecular sieves (36 g) was stirred at room temperature for 15 minutes. Ethyliodide (110 g) was added slowly at room temperature over 15 minutes. The reaction was stirred at the same temperature for a period of 15–20 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was dumped into ice water and extracted with toluene. The combined organic extracts were washed with water and the solvent was removed under reduced pressure to afford title compound of the formula (12a) (61–63 g, 80–82%).

Workup

  1. customobtained
  2. customAfter completion of the reaction
  3. extractionextracted with toluene
  4. washThe combined organic extracts were washed with water
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-44895e3756da4fc2b1a324e2706de92d
Source dataset
uspto-grants-2007_05
Patent number
US07223881B2

Reaction notes

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