Diethylaluminum chloride → HCID 21892018, compound

HRID 1826847Notes

Reaction equation

HRID 1826847 reaction equation
[CH3:1][C:2]1[C:3](=[O:23])[N:4]2[C:16](=[CH:17][C:18]=1[C:19](=[O:22])[CH2:20][CH3:21])[C:7]1=[N:8][C:9]3[C:14]([CH:15]=[C:6]1[CH2:5]2)=[CH:13][CH:12]=[CH:11][CH:10]=3.Cl[Al](CC)CC.Br[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33].[K].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>O1CCCC1.[Zn].C([O-])(=O)C.[Ag+].C(O)C>[OH:22][C:19]([C:18]1[CH:17]=[C:16]2[N:4]([CH2:5][C:6]3[C:7]2=[N:8][C:9]2[C:14]([CH:15]=3)=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3](=[O:23])[C:2]=1[CH3:1])([CH2:20][CH3:21])[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]

Participants

10

Reactant 5

HCID 7277Diethylaluminum chlorideHCID 7748Ethyl bromoacetateHCID 13355Disodium 2,3-dihydroxybutanedioateHCID 1940068-Methyl-7-propanoylindolizino[1,2-b]quinolin-9(11H)-oneHCID 5462222Potassium

Product 1

HCID 21892018HCID 21892018, compoundYield 16.6%

Reagents, catalysts & solvents 4

HCID 11246Silver acetateCatalystHCID 23994ZincCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of zinc (1.25 g, 19.1 mmol), 8-methyl-7-propionylindolizino[1,2-b]quinoline-9-(11H)-one (500 mg, 1.43 mmol, as obtained by Kingsburry, W. D., Tetrahedron Lett. 29:6847 (1988)) and silver acetate (250 mg, 1.50 mmol) in anhydrous tetrahydrofuran (10 ml) is agitated at ambient temperature under an argon atmosphere. After 10 minutes, the reaction mixture is activated by the dropwise addition of a molar solution of chlorodiethylaluminium (10 ml, 10 mmol), then ethyl bromoacetate (1.25 ml, 11.3 mmol) is added dropwise and the resultant mixture is left to react for another 5 hours. The reaction is stopped by the successive addition of ethyl alcohol (10 ml) and a saturated solution of potassium and sodium tartrate (10 ml). The resultant mixture is agitated for another hour, filtered and concentrated under reduced pressure. The residue is taken up in dichloromethane (30 ml), washed with water, dried, concentrated and purified by column chromatography (SiO2, CH2Cl2/MeOH:98/2), which produces 93 mg (1.5%) of desired product in the form of a pale yellow solid, m.p. 185–188° C.

Workup

  1. customto react for another 5 hours
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated
  7. custompurified by column chromatography (SiO2, CH2Cl2/MeOH:98/2), which

Sources & evidence

ORD record
ord-4c3de40671814d11b0d7aeae19544390
Source dataset
uspto-grants-2006_05
Patent number
US07053102B2

Reaction notes

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