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

HRID 1861539Notes

Reaction equation

[H-].[Na+].[OH:3][CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH2:25](I)[CH3:26]>CN(C)C=O>[CH2:25]([O:3][CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[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 ethyl 2-hydroxy-3-(4-benzyloxyphenyl)propionate of the formula (10) (40 g) obtained according to the procedure described in step (iii) 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 at 25-30° C. over a period of 2-3 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 the title compound 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 the reaction mixture
extractionextracted with toluene
washThe combined organic extracts were washed with water
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-a7d090d76e2b40b8bbf916bb652c3a3c
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06531596B1

Reaction notes

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