1-Heptyne → HCID 4663481, compound

HRID 1776452Notes

Reaction equation

HRID 1776452 reaction equation
[Na].[CH:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:9](Cl)(=[O:12])[CH2:10][CH3:11]>COCCOCCOC.C(OCC)C>[CH3:11][CH2:10][C:9](=[O:12])[C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 123501-HeptyneHCID 62324Propionyl chlorideHCID 5360545Sodium2×

Product 1

HCID 4663481HCID 4663481, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8150DiglymeSolvent2×

Conditions

Temperature
27.5 °C

Procedure

A 1-liter reactor was loaded with 345 mL of diglyme (RN 111-96-6) and 17.2 g (748 mmoles) of sodium (RN 7440-23-5) cut into pieces. After heating to a temperature slightly above the melting point of sodium accompanied by thorough stirring, 71.7 g (745 mmoles) i.e. 97.5 mL of 1-heptyne (RN 628-71-7) in solution in 100 mL of diglyme is then added four times at hourly intervals. The medium thickens to form a beige suspension. Stirring is continued for another 2 hours 30 minutes at the same temperature. The mixture is cooled down to 25-30° C. and poured slowly into a stirred solution of 64.8 g (700 mmoles) i.e. 61.0 mL of propionyl chloride (RN 79-03-8) in 600 mL of ethyl ether. An exothermic reaction takes place followed by stirring for 1 hour at no particular temperature.

Workup

  1. additionis then added four times at hourly intervals
  2. customto form a beige suspension
  3. customAn exothermic reaction
  4. stirringby stirring for 1 hour at no particular temperature

Sources & evidence

ORD record
ord-38c0e2f352b648e7aac24b9446acdb60
Source dataset
uspto-grants-2016_02
Patent number
US09265852B2

Reaction notes

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