Hydrochloric Acid → HCID 20553971, compound

HRID 1106296Notes

Reaction equation

HRID 1106296 reaction equation
[CH:1]([Mg]Cl)=[CH2:2].[CH:5]#[C:6][CH2:7][C:8](=[O:14])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].Cl>CCOCC>[CH:1]([C:8]([OH:14])([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:7][C:6]#[CH:5])=[CH2:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 205539671-Nonyn-4-oneHCID 178461836HCID 178461836, compound

Product 1

HCID 20553971HCID 20553971, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of 130 ml of 2.3 molar vinyl magnesium chloride in 100 ml of ether is cooled to 0° and treated dropwise with 14 g of 1-nonyn-4-one in 50 ml of ether. The reaction mixture is allowed to come to room temperature and poured into ether and dilute hydrochloric acid. The organic layer is separated, washed with water, dried over sodium sulfate, stripped of solvent and the residue is chromatographed on silica gel with 20% ethyl acetate in hexane as eluent to give the title product.

Workup

  1. customto come to room temperature
  2. customThe organic layer is separated
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customthe residue is chromatographed on silica gel with 20% ethyl acetate in hexane as eluent

Sources & evidence

ORD record
ord-c7b65e94a1724acbb40e216a0bdac2b4
Source dataset
uspto-grants-1982_01
Patent number
US04312994

Reaction notes

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