Hydrochloric Acid → HCID 11126559, compound

HRID 1967423Notes

Reaction equation

HRID 1967423 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:4])[CH2:2][CH3:3].[C:11]([Mg]Br)#[CH:12].Cl.C(OCC)C>C1COCC1>[C:5]1([C:1]([OH:4])([CH2:11][CH3:12])[C:2]#[CH:3])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 71481-Phenyl-1-propanoneHCID 178418486HCID 178418486, compound

Product 1

HCID 11126559HCID 11126559, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of propiophenone in THF (0.2 ml, 1.505 mmol) is slowly added dropwise at room temperature with stirring to a solution of ethynylmagnesium bromide (4 ml, 2.0 mmol, 0.5 M in THF) in THF (5 ml). The slightly yellow reaction solution was stirred at RT for 1 h. The reaction mixture is acidified using 1N HCl, during which a turbidity initially formed which disappeared with an increase in the pH into the acidic region. Diethyl ether was added to the solution, the aqueous phase was separated off, and the organic phase was extracted once with water. The organic phase was dried using sodium sulfate, filtered off and evaporated to dryness, giving 3-phenylpent-1-yn-3-ol (233 mg, 0.001 mol) in 65% yield. The crude mixture is reacted further without further purification.

Workup

  1. customduring which a turbidity initially formed which
  2. temperaturean increase in the pH into the acidic region
  3. customthe aqueous phase was separated off
  4. extractionthe organic phase was extracted once with water
  5. customThe organic phase was dried
  6. filtrationfiltered off
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-da0e7be4491a48cca22f0ee76c1a97e6
Source dataset
uspto-grants-2013_04
Patent number
US08420820B2

Reaction notes

Loading…