Potassium tert-butoxide → HCID 57633833, compound

HRID 251720Notes

Reaction equation

HRID 251720 reaction equation
Br[CH:2](Br)[CH2:3][C:4]12[CH2:14][C:8]3([CH3:15])[CH2:9][C:10]([CH3:13])([CH2:12][C:6]([C:16]45[CH2:26][C:20]6([CH3:27])[CH2:21][C:22]([CH3:25])([CH2:24][C:18]([CH2:28][CH:29](Br)Br)([CH2:19]6)[CH2:17]4)[CH2:23]5)([CH2:7]3)[CH2:5]1)[CH2:11]2.CC(C)([O-])C.[K+]>O>[C:3]([C:4]12[CH2:11][C:10]3([CH3:13])[CH2:9][C:8]([CH3:15])([CH2:7][C:6]([C:16]45[CH2:26][C:20]6([CH3:27])[CH2:21][C:22]([CH3:25])([CH2:24][C:18]([C:28]#[CH:29])([CH2:19]6)[CH2:17]4)[CH2:23]5)([CH2:12]3)[CH2:5]1)[CH2:14]2)#[CH:2]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 57934734HCID 57934734, compound

Product 1

HCID 57633833HCID 57633833, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Next, 63.4 g of the 3,3′-bis(2,2′-dibromoethyl)-5,5′,7,7′-tetramethyl-1,1′-biadamantane obtained above (90.9 mmol), 200 ml of N,N-dimethylsulfoxide and a stirrer were charged in a 500 mL recovery flask. Under nitrogen flow, 28 g of potassium tert-butoxide (250 mmol) was added with agitating at room temperature. After the addition, the mixture was agitated at room temperature for 48 hours. Reaction solution was added to 400 mL of ion-exchange water. An aqueous layer was separated and removed therefrom, and solvent was removed under reduced pressure. Solid thus obtained was dried under reduced pressure, thus obtaining 31.5 g of 3,3′-diethynyl-5,5′,7,7′-tetramethyl-1,1′-biadamantane (84.1 mmol; yield: 92.5%).

Workup

  1. additionwere charged in a 500 mL recovery flask
  2. additionAfter the addition
  3. stirringthe mixture was agitated at room temperature for 48 hours
  4. customReaction solution
  5. customAn aqueous layer was separated
  6. customremoved
  7. customsolvent was removed under reduced pressure
  8. customSolid thus obtained
  9. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-40b10bd34de24b3caa93c5e8a583a974
Source dataset
uspto-grants-2011_01
Patent number
US07863347B2

Reaction notes

Loading…