Diethyl Ether → HCID 518949, compound

HRID 2195587Notes

Reaction equation

HRID 2195587 reaction equation
[Mg].C(OCC)C.[CH2:7](Br)[CH2:8][CH2:9][CH3:10].Br[C:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2>ClCCl.O>[CH2:7]([C:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2)[CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 3283Diethyl Ether3×HCID 8002Butyl bromideHCID 791061-BromoadamantaneHCID 5462224Magnesium

Product 1

HCID 518949HCID 518949, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Into a 1 liter egg plant-shaped flask, 4.9 g (0.2 moles) of magnesium was weighed and placed. Under the stream of nitrogen gas, 80 ml of diethyl ether was added and stirred. Then, a solution prepared by dissolving 27.4 g (0.2 moles) of n-butyl bromide into 20 ml of diethyl ether was added dropwise. After the addition was completed, the resultant mixture was heated under the refluxing condition for 30 minutes. The temperature was adjusted at the room temperature, and diethyl ether was completely removed using a vacuum pump. Then, a solution prepared by dissolving 21.5 g (0.1 mole) of 1-bromoadamantane into 300 ml of dichloromethane was added dropwise. After the addition was completed, the resultant mixture was heated under the refluxing condition for 5 hours. The reaction fluid was poured into 200 ml of ion-exchanged water and treated by extraction with dichloromethane using a separation funnel. The solvent was removed using an evaporator. The residue was dissolved into 20 ml of hexane and purified in accordance with the silica gel column chromatography (the solvent of development: hexane). The solvent was removed using an evaporator, and 7.3 g of 1-(n-butyl)-adamantane was obtained as a colorless transparent liquid substance (the yield: 38%).

Workup

  1. customThen, a solution prepared
  2. additionwas added dropwise
  3. additionAfter the addition
  4. customwas completely removed
  5. customThen, a solution prepared
  6. additionwas added dropwise
  7. additionAfter the addition
  8. customThe solvent was removed
  9. customan evaporator
  10. dissolutionThe residue was dissolved into 20 ml of hexane
  11. custompurified in accordance with the silica gel column chromatography (the solvent of development
  12. customThe solvent was removed
  13. customan evaporator

Sources & evidence

ORD record
ord-8fa75f6a8941458d85bc8d391ded6ca9
Source dataset
uspto-grants-2012_12
Patent number
US08337982B2

Reaction notes

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