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Ethyl benzoylacetate → HCID 22664979, compound

HRID 392588
Notes
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Reaction equation

HRID 392588 reaction equation
I[CH:2]([CH3:6])[CH:3](I)[CH3:4].C(=O)([O-])[O-].[Na+].[Na+].[CH2:13]([O:15][C:16](=[O:26])[CH2:17][C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:14]>CN(C)C=O>[C:18]([C:17]1([C:16]([O:15][CH2:13][CH3:14])=[O:26])[CH2:4][CH2:3][CH2:2][CH2:6]1)(=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7170Ethyl benzoylacetateHCID 10340Sodium CarbonateHCID 230423272,3-Diiodobutane

Product 1

HCID 22664979HCID 22664979, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
57.5 °C

Procedure

Diiodobutane (17.1 g, 55 mmol), sodium carbonate (35 g, 330 mmol), ethylbenzoylacetate (10.6 g, 55 mmol) and dimethylformamide (170 ml) were mixed and the mixture was stirred at 55 to 60° C. overnight. The mixture after completion of reaction was poured into ice water and the mixture was extracted twice with ethyl acetate (100 ml). The extract was dried over sodium sulfate, and after concentration, purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give the title compound (7.9 g, 58%) as a colorless oil.

Workup

  1. customThe mixture after completion of reaction
  2. extractionthe mixture was extracted twice with ethyl acetate (100 ml)
  3. dry with materialThe extract was dried over sodium sulfate
  4. concentrationafter concentration
  5. custompurified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-df9244668d0f45f2a8310bb2a704043d
Source dataset
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06800778B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes