Ammonium Chloride → HCID 389880, compound

HRID 983773Notes

Reaction equation

HRID 983773 reaction equation
[CH3:1][Li].[C:3]([C:8]([C:17]([O:19][CH2:20][CH3:21])=[O:18])([CH2:14][CH:15]=[CH2:16])[CH2:9][CH2:10][C:11](Cl)=[O:12])([O:5][CH2:6][CH3:7])=[O:4].[Cl-].[NH4+]>[Cu](I)I.CCOCC>[C:3]([C:8]([C:17]([O:19][CH2:20][CH3:21])=[O:18])([CH2:14][CH:15]=[CH2:16])[CH2:9][CH2:10][C:11](=[O:12])[CH3:1])([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 10517649HCID 10517649, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 389880HCID 389880, compoundYield 109.1%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ether suspension (2 ml) containing copper iodide (0.293 g, 1.2 mmol) was added dropwise at −10° C. 1.26 ml of 1.91M ether solution containing methyl lithium (2.4 mmol). After heating to 0° C. over 30 minutes, the reaction liquid was given 4,4-dicarboethoxy-6-heptenic acid chloride (0.291 g, 1.0 mmol), followed by stirring at 0° C. for 6 hours. After addition of a saturated aqueous solution of ammonium chloride, the reaction liquid was extracted with ether. The organic layer was dried with anhydrous magnesium sulfate and freed of solvent by vacuum distillation. The residues were purified by silica gel chromatography to give 0.295 g of 5,5-dicarboethoxy-7-octen-2-on (yields: 91%). Characteristic Values of 5,5-dicarboethoxy-7-octen-2-on

Workup

  1. additionwas added dropwise at −10° C
  2. customthe reaction liquid
  3. customthe reaction liquid
  4. extractionwas extracted with ether
  5. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  6. distillationfreed of solvent by vacuum distillation
  7. customThe residues were purified by silica gel chromatography

Sources & evidence

ORD record
ord-46ddfc58f98f457dbba8cb7f873a5333
Source dataset
uspto-grants-2005_03
Patent number
US06867161B1

Reaction notes

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