Methyl iodide → 1-isopropyladamantane

HRID 346095Notes

Reaction equation

HRID 346095 reaction equation
[Mg].[CH3:2]I.[CH3:4][C:5](O)=O.[CH:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2.[Cl-].[NH4+]>CCOCC>[CH:5]([C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5462224Magnesium2×HCID 21868329HCID 21868329, compound

Product 1

HCID 5244831-isopropyladamantaneYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

Introduce 0.5 mol of magnesium chips into 50 ml of absolute ether, and drop 0.5 mol of methyl iodide into the solution under moisture-free conditions until the ether boils. Subsequently, heat in a water bath until the magnesium has completely dissolved. Into this solution at room temperature drop 0.2 mol of adamantane methyl carboxylate in absolute ether. Then heat to reflux for 3 hours. After cooling, hydrolize with ice and mix with ammonium chloride solution until the precipitate has dissolved. Separate the ether phase, wash the aqueous phase with 2 portions of ether, and wash the combined organic phases with sodium bicarbonate solution. Then dry and evaporate to dryness under vacuum. (Yield: 93%).

Workup

  1. dissolutionhas completely dissolved
  2. customat room temperature
  3. temperatureThen heat
  4. temperatureto reflux for 3 hours
  5. temperatureAfter cooling, hydrolize with ice
  6. dissolutionhas dissolved
  7. customSeparate the ether phase
  8. washwash the aqueous phase with 2 portions of ether
  9. washwash the combined organic phases with sodium bicarbonate solution
  10. customThen dry
  11. customevaporate to dryness under vacuum

Sources & evidence

ORD record
ord-20d4c3dfad2d4bdda7b92634ed5913ba
Source dataset
uspto-grants-1991_10
Patent number
US05061703

Reaction notes

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