Diethyl Ether → HCID 15529887, compound

HRID 2195589Notes

Reaction equation

HRID 2195589 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][C:15]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:16]3)[CH2:14]1)[CH2:20]2>ClCCl.O>[CH2:7]([C:19]12[CH2:20][CH:13]3[CH2:22][CH:17]([CH2:16][C:15]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:14]3)[CH2:21]1)[CH2:18]2)[CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 3283Diethyl Ether3×HCID 8002Butyl bromideHCID 5462224MagnesiumHCID 15529886HCID 15529886, compound

Product 1

HCID 15529887HCID 15529887, compoundYield 33%

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 27.1 g (0.1 mole) of 1-bromo-3-(n-butyl)adamantane obtained in accordance with the process described above in 1-2) 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 8.20 g of 1,3-di(n-butyl)adamantane of the object compound was obtained (the yield: 33%).

Workup

  1. customThen, a solution prepared
  2. additionwas added dropwise
  3. additionAfter the addition
  4. customwas completely removed
  5. customThen, a solution prepared
  6. customobtained in accordance with the process
  7. additionwas added dropwise
  8. additionAfter the addition
  9. customThe solvent was removed
  10. customan evaporator
  11. dissolutionThe residue was dissolved into 20 ml of hexane
  12. custompurified in accordance with the silica gel column chromatography (the solvent of development
  13. customThe solvent was removed
  14. customan evaporator, and 8.20 g of 1,3-di(n-butyl)adamantane of the object compound
  15. customwas obtained (the yield: 33%)

Sources & evidence

ORD record
ord-cddcc749177e494cac89faee103031ad
Source dataset
uspto-grants-2012_12
Patent number
US08337982B2

Reaction notes

Loading…