Hydrochloric Acid → HCID 57481298, compound

HRID 860408Notes

Reaction equation

HRID 860408 reaction equation
[Cl-].[Mg+2].[Cl-].[C:4]([CH:7]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])(=[O:6])[CH3:5].[C:24]([C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29](Cl)=[O:30])#[N:25].Cl>ClCCl.C(OCC)(=O)C.N1C=CC=CC=1>[C:4]([C:7]([C:29](=[O:30])[C:28]1[CH:32]=[CH:33][CH:34]=[C:26]([C:24]#[N:25])[CH:27]=1)([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])(=[O:6])[CH3:5]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3084833-Cyanobenzoyl chlorideHCID 5360315Magnesium ChlorideHCID 574812961-Tert-butyl 7-ethyl 2-acetylheptanedioate

Product 1

HCID 57481298HCID 57481298, compoundYield 72.9%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of magnesium chloride (1.33 g) in dichloromethane (40 mL) was added 1-tert-butyl 7-ethyl 2-acetylheptanedioate (4.0 g) at ambient temperature under N2. To this mixture was added dropwise pyridine (2.26 mL) in an ice-water bath. Then the mixture was stirred at ambient temperature for 40 minutes. To the reaction mixture was added a solution of 3-cyanobenzoyl chloride (3.01 g) in dichloromethane (6 mL) dropwise over 2 minutes. The reaction mixture was stirred at ambient temperature for 2 hours. To the mixture was added 1N hydrogen chloride and ethyl acetate in an ice-water bath. The organic layer was washed with 1N hydrogen chloride, water, and brine, dried over magnesium sulfate, and evaporated in vacuo to give a solid. The residue was purified by flash silica gel chromatography (silica gel, 300 mL) eluting with hexane-ethyl acetate=10-1, 8-1, 5-1, and 3-1 to give 1-tert-butyl 7-ethyl 2-acetyl-2-(3-cyanobenzoyl)heptanedioate (4.23 g, 72.9%) as colorless oil.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 2 hours
  2. washThe organic layer was washed with 1N hydrogen chloride, water, and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customto give a solid
  6. customThe residue was purified by flash silica gel chromatography (silica gel, 300 mL)
  7. washeluting with hexane-ethyl acetate=10-1, 8-1, 5-1, and 3-1

Sources & evidence

ORD record
ord-a1a3cad103e24cf59ee891719627d7cb
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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