HCID 22269459, compound → HCID 22269464, compound

HRID 983736Notes

Reaction equation

HRID 983736 reaction equation
[CH:1]([C:5]1[CH:6]=[CH:7][C:8]2[CH2:9][C:10]3[C:23]([C:24](=O)[C:25]=2[CH:26]=1)=[CH:22][C:21]1[CH2:20][C:19]2[C:14](=[CH:15][C:16]([CH:28]([CH2:30][CH3:31])[CH3:29])=[CH:17][CH:18]=2)[C:13](=O)[C:12]=1[CH:11]=3)([CH2:3][CH3:4])[CH3:2]>COCCOCCOC>[CH:1]([C:5]1[CH:6]=[CH:7][C:8]2[C:25](=[CH:24][C:23]3[C:10]([CH:9]=2)=[CH:11][C:12]2[C:21](=[CH:20][C:19]4[C:14]([CH:13]=2)=[CH:15][C:16]([CH:28]([CH2:30][CH3:31])[CH3:29])=[CH:17][CH:18]=4)[CH:22]=3)[CH:26]=1)([CH2:3][CH3:4])[CH3:2]

Participants

3

Reactant 1

HCID 22269459HCID 22269459, compound

Product 1

HCID 22269464HCID 22269464, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2 grams of 3,10-di-sec-butyl-7,14-dihydropentacene-5,12-dione and 45.3 mL of 2-methoxyethyl ether was stirred and flushed with nitrogen for 15 minutes. To this was added 1.52 grams of sodium borohydride and the mixture was heated to 60° C. overnight. The mixture was cooled to room temperature. To the mixture was added 0.4 grams of sodium borohydride and stirring was continued for 30 mintues. To the mixture was added 15 mL of isopropyl alcohol and stirring was continued at room temperature for 5 hours. To the mixture was added 15 mL of methanol. To the mixture was added 1.0 grams of sodium borohydride and stirring was continued at room temperature. To the mixture was added 16 mL of acetic acid and the mixture was heated to 60° C. for one hour. To the mixture was added 16 mL of concentrated hydrochloric acid and heating was continued at 60° C. The resulting solid was collected by filtration and washed with water followed by ethyl acetate and then acetone. The solid was dried to give 2,9-di-sec-butylpentacene.

Workup

  1. customflushed with nitrogen for 15 minutes
  2. additionTo this was added 1.52 grams of sodium borohydride
  3. temperatureThe mixture was cooled to room temperature
  4. additionTo the mixture was added 0.4 grams of sodium borohydride
  5. stirringstirring
  6. additionTo the mixture was added 15 mL of isopropyl alcohol
  7. stirringstirring
  8. additionTo the mixture was added 15 mL of methanol
  9. additionTo the mixture was added 1.0 grams of sodium borohydride
  10. stirringstirring
  11. customwas continued at room temperature
  12. additionTo the mixture was added 16 mL of acetic acid
  13. temperaturethe mixture was heated to 60° C. for one hour
  14. additionTo the mixture was added 16 mL of concentrated hydrochloric acid
  15. temperatureheating
  16. customwas continued at 60° C
  17. filtrationThe resulting solid was collected by filtration
  18. washwashed with water
  19. customThe solid was dried

Sources & evidence

ORD record
ord-28b5d6457f5c4657aa0ec4479ef206e6
Source dataset
uspto-grants-2005_03
Patent number
US06864396B2

Reaction notes

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