Water → 3,3',5,5'-Tetraethynyl-1,1'-biadamantane

HRID 39116Notes

Reaction equation

HRID 39116 reaction equation
Br[CH:2](Br)[CH2:3][C:4]12[CH2:17][CH:8]3[CH2:9][C:10]([CH2:13][CH:14](Br)Br)([CH2:12][C:6]([C:18]45[CH2:27][C:22]6([CH2:28][CH:29](Br)Br)[CH2:23][CH:24]([CH2:26][C:20]([CH2:32][CH:33](Br)Br)([CH2:21]6)[CH2:19]4)[CH2:25]5)([CH2:7]3)[CH2:5]1)[CH2:11]2.CC(C)([O-])C.[K+].O>CS(C)=O>[C:28]([C:22]12[CH2:23][CH:24]3[CH2:26][C:20]([C:32]#[CH:33])([CH2:19][C:18]([C:6]45[CH2:5][C:4]6([C:3]#[CH:2])[CH2:17][CH:8]([CH2:9][C:10]([C:13]#[CH:14])([CH2:11]6)[CH2:12]4)[CH2:7]5)([CH2:25]3)[CH2:27]1)[CH2:21]2)#[CH:29]

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 866374533,3',5,5'-Tetra(dibromoethyl)-1,1'-biadamantane

Product 1

HCID 576338403,3',5,5'-Tetraethynyl-1,1'-biadamantane

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The obtained 3,3′,5,5′-tetrakis(dibromoethyl)-1,1′-biadamantane was dissolved in 200 ml of dimethyl sulfoxide, and then 28 g (250 mmol) of potassium tert-butoxide was added at room temperature and the mixture was stirred for 48 hours. The reaction mixture was added to 400 ml of water, the mixture was extracted 3 times using 200 ml of dichloromethane each time and then washed with 200 ml of water and dried over magnesium sulfate, and the organic layer was concentrated to obtain 11.0 g of 3,3′,5,5′-tetraethynyl-1,1′-biadamantane.

Workup

  1. extractionthe mixture was extracted 3 times
  2. washwashed with 200 ml of water
  3. dry with materialdried over magnesium sulfate
  4. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-6294eb65208c4c79a866142ac3026353
Source dataset
uspto-grants-2013_09
Patent number
US08524847B2

Reaction notes

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