HCID 22269459, compound → HCID 22269464, compound

HRID 488964Notes

Reaction equation

HRID 488964 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 minutes. 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 one gram 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 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. waitwas continued at room temperature for 5 hours
  9. additionTo the mixture was added 15 mL of methanol
  10. additionTo the mixture was added one gram of sodium borohydride
  11. stirringstirring
  12. customwas continued at room temperature
  13. additionTo the mixture was added 16 mL of acetic acid
  14. temperaturethe mixture was heated to 60° C. for one hour
  15. additionTo the mixture was added 16 mL of concentrated hydrochloric acid
  16. temperatureheating
  17. customwas continued at 60° C
  18. filtrationThe solid was collected by filtration
  19. washwashed with water
  20. customThe solid was dried

Sources & evidence

ORD record
ord-ec1c507ee72841b1be8a16370e98a51a
Source dataset
uspto-grants-2005_12
Patent number
US06974877B2

Reaction notes

Loading…