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

HRID 1354904Notes

Reaction equation

HRID 1354904 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:24])[CH:7]([OH:23])[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)[CH3:4].[CH2:25](I)[CH3:26]>CN(C)C=O>[CH2:25]([O:23][CH:7]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:11][CH:10]=1)[C:6]([O:5][CH2:3][CH3:4])=[O:24])[CH3:26]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 151861533-(4-Benzyloxyphenyl)-2-hydroxypropionic acid ethyl ester2×

Product 1

HCID 110779683-(4-Benzyloxyphenyl)-2-ethoxypropanoic acid ethyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a slurry of sodium hydride (60% suspension in oil, 7.5 g), and dimethyl formamide (70 ml) was added a solution of the racemic ethyl-2-hydroxy-3-(4-benzyloxyphenyl)propionate of the formula (10) (40 g) obtained according to the procedure described in step (iv) above in dimethylformide (105 ml) at 5–10° C. over a period of 15–30 minutes. The temperature was allowed to attain room temperature and maintained at the same temperature for 1–3 h. Ethyl iodide (36 g) was added slowly by maintaining the temperature at 25–30° C. over a period of 2–3 hours. 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 racemic 2-ethoxy ethyl ester of the formula (12a) (47–48 g, 98–99%).

Workup

  1. customobtained
  2. waitdescribed in step (iv) above in dimethylformide (105 ml) at 5–10° C. over a period of 15–30 minutes
  3. customto attain room temperature
  4. temperaturemaintained at the same temperature for 1–3 h
  5. temperatureby maintaining the temperature at 25–30° C. over a period of 2–3 hours
  6. customAfter completion of the reaction
  7. extractionextracted with toluene
  8. washThe combined organic extracts were washed with water
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7f78222636604150a6a0493104b623e0
Source dataset
uspto-grants-2007_05
Patent number
US07223881B2

Reaction notes

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