Hydrochloric Acid → 10-Phthalimido-3-oxo-5,8-dioxadecanoic acid ethyl ester

HRID 1608256Notes

Reaction equation

[C:1]1(=[O:17])[N:5]([CH2:6][CH2:7][O:8][CH2:9][CH2:10][OH:11])[C:4](=[O:12])[C:3]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:2]12.[H-].[Na+].Cl[CH2:21][C:22](=[O:29])[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].Cl>O1CCCC1>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][C:22](=[O:29])[CH2:21][O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][N:5]1[C:4](=[O:12])[C:3]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:2]2[C:1]1=[O:17])[CH3:28]

Participants

Conditions

Temperature: 25 °C

Procedure

77 g of 2-[2-(phthalimido)ethoxy]ethanol are added, in portions, to a suspension of 31 g of sodium hydride in 400 ml of tetrahydrofuran, while maintaining the temperature in the vicinity of 25° C. The mixture is stirred for one hour and 53.6 g of ethyl chloroacetoacetate are then added, while maintaining the temperature of the mixture at -20° C. The mixture is allowed to stand overnight at ambient temperature and then hydrolyzed with 1 l of 1N hydrochloric acid. Decantation, followed by extraction with ether are carried out and the organic phases are combined. The combined organic phase is washed with water and then dried over magnesium sulfate. It is concentrated and the residue thereby obtained (110 g) is purified by silica column chromatography using a dichloromethane:acetone (95:5) mixture as the eluting solvent.

Workup

temperaturewhile maintaining the temperature of the mixture at -20° C
waitto stand overnight at ambient temperature
extractionDecantation, followed by extraction with ether
washThe combined organic phase is washed with water
dry with materialdried over magnesium sulfate
concentrationIt is concentrated
customthe residue thereby obtained (110 g)
customis purified by silica column chromatography

Sources & evidence

ORD record: ord-7009cdbb16064946ae3470c9367a7959
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04870091

Reaction notes

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