Tetrahydrofuran → HCID 21889343, compound

HRID 720231Notes

Reaction equation

HRID 720231 reaction equation
C1COCC1.[C:6]1([C:12]2[C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:22](=O)[C:23]5[CH:34]=[C:33]([C:35]6[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=6)[C:26]6=[CH:27][CH:28]=[CH:29][C:30]7[C:31](=O)[C:14](=[C:15]([C:24]=5[C:25]=76)[C:16]=34)[CH:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CO>[C:6]1([C:12]2[C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[CH:22]=[C:23]5[CH:34]=[C:33]([C:35]6[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=6)[C:26]6=[CH:27][CH:28]=[CH:29][C:30]7[CH:31]=[C:14]([C:15]([C:16]=34)=[C:24]5[C:25]=76)[CH:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 21889342HCID 21889342, compound

Product 1

HCID 21889343HCID 21889343, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a 1 L of three neck flask with nitrogen protected condenser were charged with 500 mL of anhydrous tetrahydrfuran (THF) containing 9.2 g (0.02 mol.) of 4,10-Diphenyl-dibenzo[def,mno]chrysene-6,12-dione. Then 20 mL of 1.0 M of boran etherate was added by syringe slowly to above solution. The reaction mixture was slowly warm to 70° C. while stirring until the reaction mixture change to a completely pale yellow solution and then another 5 mL of 0.1.0 M of boran etherate was added by syringe. The reaction was continued for another 1 hour at 70° C. The reaction mixture was cooled to room temperature and 15 mL of methanol was slowly added to quench the excess boran agent. After the bubbles were ceased, the solvents were removed with a rotary evaporator. The residue was added to 20 mL of ethanol and the precipitates were filtered and dried. The 6.4 g of pure 4,10-Diphenyl-dibenzo[def,mno]chrysene was obtained by nitrogen flow sublimation at 275˜285° C. under 2 torr vacuum. Yield is in 74.8%.

Workup

  1. additionThen 20 mL of 1.0 M of boran etherate was added by syringe slowly to above solution
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customto quench the excess boran agent
  4. customthe solvents were removed with a rotary evaporator
  5. additionThe residue was added to 20 mL of ethanol
  6. filtrationthe precipitates were filtered
  7. customdried

Sources & evidence

ORD record
ord-d57597991d33448aa4232febc701448e
Source dataset
uspto-grants-2006_11
Patent number
US07135243B2

Reaction notes

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