Toluene → HCID 20541527, compound

HRID 126705Notes

Reaction equation

HRID 126705 reaction equation
[Mg].CC[O:4]CC.[CH2:7](Br)[C:8]#[CH:9].[NH4+].[Cl-:12].[C:13]1(C)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>Cl[Hg]Cl>[Cl:12][CH2:9][CH2:8][CH2:7][C:13]([OH:4])([CH:18]=[CH2:17])[CH2:14][C:15]#[CH:16]

Participants

7

Reactant 5

HCID 1140TolueneHCID 3283Diethyl Ether3×HCID 7842Propargyl bromide2×HCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 20541527HCID 20541527, compound

Reagents, catalysts & solvents 1

HCID 24085Mercuric ChlorideCatalyst

Conditions

Temperature
0 °C

Procedure

To a suspension of 3.0 g. (0.12 mol.) of magnesium metal in 10 ml. ether containing 100 mg. HgCl2 is added with stirring, under argon, 0.3 ml. of CH2CH2B2. After 5 minutes a reaction is initiated and 0.5 g. of 80% propargylbromide in toluene is added. Upon evidence of a vigorous reaction, an additional 25 ml. of ether is introduced. A mixture of 13 g. (0.1 mol) of 7-chlorohept-1-en-2-one and 19.5 g. (0.12 mol.) of propargylbromide in 35 ml. ether is added at such a rate to maintain a vigorous reflux. After addition is complete, stirring is continued 10 minutes. The mixture is cooled to 0° C. and satd. NH4Cl is added slowly. The mixture is filtered through diatomaceous earth and the ether is removed in vacuo to provide the title product as an oil.

Workup

  1. additionTo a suspension of 3.0 g
  2. customUpon evidence of a vigorous reaction
  3. additionA mixture of 13 g
  4. temperatureto maintain a vigorous reflux
  5. additionAfter addition
  6. stirringstirring
  7. waitis continued 10 minutes
  8. filtrationThe mixture is filtered through diatomaceous earth
  9. customthe ether is removed in vacuo

Sources & evidence

ORD record
ord-eb13827f2dfd4752befd195e39bd0660
Source dataset
uspto-grants-1981_03
Patent number
US04254036

Reaction notes

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