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

HRID 1861549Notes

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

Conditions

Temperature: 27.5 °C

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 ethyl2-hydroxy-3-(4-benzyloxy phenyl)propionate of the formula (10) (40 g) obtained according to the procedure described in step (iv) above in dimethylformamide (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 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

customobtained
customto attain room temperature
temperaturemaintained at the same temperature for 1-3 h
customAfter completion of the reaction
extractionextracted with toluene
washThe combined organic extracts were washed with water
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-5595f5d3a90d483f83b46d35138e9b71
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06531596B1

Reaction notes

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