Potassium Carbonate → HCID 86665361, compound

HRID 535301Notes

Reaction equation

HRID 535301 reaction equation
[C:1]1([C:11]2[C:23]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16]4([C:35]5[C:34](OC)=[CH:33][CH:32]=[C:31]([C:38]6[C:47]7[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=7)[CH:41]=[CH:40][CH:39]=6)[C:30]=5[C:29]5[C:24]4=[CH:25][CH:26]=[CH:27][CH:28]=5)[C:15]=3[C:14](OC)=[CH:13][CH:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1(N2C(Cl)=NN=N2)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:38]1([C:31]2[C:30]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:16]4([C:15]5[CH:14]=[CH:13][CH:12]=[C:11]([C:1]6[C:10]7[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=7)[CH:4]=[CH:3][CH:2]=6)[C:23]=5[C:22]5[C:17]4=[CH:18][CH:19]=[CH:20][CH:21]=5)[C:35]=3[CH:34]=[CH:33][CH:32]=2)[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 842621H-Tetrazole, 5-chloro-1-phenyl-HCID 69669040HCID 69669040, compound

Product 1

HCID 86665361HCID 86665361, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

A well-stirred suspension of 31.5 g (50 mmol) of 4,4′-bis(naphth-1-yl)-1,1′-dimethoxy-9,9′-spirobifluorene, 18.1 g (100 mmol) of 1-phenyl-5-chloro-tetrazole and 27.6 g (200 mmol) of K2CO3 is heated under reflux for 18 h in 250 ml of acetone. After cooling, the precipitated solid is filtered off with suction and dried. The solid is dissolved in 200 ml of toluene, 6 g of 5% Pd/C are added, and the mixture is stirred at 40° C. for 8 h under a hydrogen atmosphere. After removal of the solvent, the residue is washed three times with 50 ml of ethanol:water (1:1, v:v) and three times with 100 ml of ethanol and subsequently recrystallised three times from DMF (about 10 ml/g). Yield: 18.7 g (33 mmol), 69.0%, purity: 99.9% (HPLC).

Workup

  1. temperatureis heated
  2. temperatureAfter cooling
  3. filtrationthe precipitated solid is filtered off with suction
  4. customdried
  5. dissolutionThe solid is dissolved in 200 ml of toluene
  6. addition6 g of 5% Pd/C are added
  7. customAfter removal of the solvent
  8. washthe residue is washed three times with 50 ml of ethanol:water (1:1, v:v) and three times with 100 ml of ethanol
  9. customsubsequently recrystallised three times from DMF (about 10 ml/g)

Sources & evidence

ORD record
ord-630a8e8d7abe4b158df8ef8cb81fd5a5
Source dataset
uspto-grants-2014_10
Patent number
US08859111B2

Reaction notes

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