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

HRID 703655
Notes
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Reaction equation

HRID 703655 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 69484Ethyl 4-chloroacetoacetateHCID 27554062-(2-(2-Hydroxyethoxy)ethyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 1412661710-Phthalimido-3-oxo-5,8-dioxadecanoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

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. After removing the eluting solvent, 35.7 g of 10-phthalimido-3-oxo-5,8-dioxadecanoic acid ethyl ester are obtained.

Workup

  1. temperaturewhile maintaining the temperature of the mixture at -20° C
  2. waitto stand overnight at ambient temperature
  3. extractionDecantation, followed by extraction with ether
  4. washThe combined organic phase is washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationIt is concentrated
  7. customthe residue thereby obtained (110 g)
  8. customis purified by silica column chromatography
  9. customAfter removing the eluting solvent, 35.7 g of 10-phthalimido-3-oxo-5,8-dioxadecanoic acid ethyl ester
  10. customare obtained

Sources & evidence

ORD record
ord-245dfa84df4e493ca754d84d4cd1006a
Source dataset
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04983740

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes