Hydrochloric Acid → HCID 20553971, compound
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
Product 1
Reagents, catalysts & solvents 1
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
- customto come to room temperature
- customThe organic layer is separated
- washwashed with water
- dry with materialdried over sodium sulfate
- 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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