HCID 22269441, compound → HCID 22269447, compound

HRID 488962Notes

Reaction equation

HRID 488962 reaction equation
[CH2:1]1[C:30]2[C:5](=[CH:6][C:7]3[C:8](=O)[C:9]4[C:26]([CH2:27][C:28]=3[CH:29]=2)=[CH:25][C:24]2[C:23](=O)[C:22]3[C:13](=[CH:14][C:15]5[CH2:16][CH2:17][CH2:18][CH2:19][C:20]=5[CH:21]=3)[CH2:12][C:11]=2[CH:10]=4)[CH2:4][CH2:3][CH2:2]1.C1C2C(=CC3C(=O)C4C(CC=3C=2)=CC2CC3C(=CC5CCCCC=5C=3)C(=O)C=2C=4)CCC1>COCCOCCOC>[CH2:16]1[C:15]2[C:20](=[CH:21][C:22]3[C:13]([CH:14]=2)=[CH:12][C:11]2[C:24](=[CH:25][C:26]4[C:9]([CH:10]=2)=[CH:8][C:7]2[C:28](=[CH:29][C:30]5[CH2:1][CH2:2][CH2:3][CH2:4][C:5]=5[CH:6]=2)[CH:27]=4)[CH:23]=3)[CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 22269441HCID 22269441, compoundHCID 22269458HCID 22269458, compound

Product 1

HCID 22269447HCID 22269447, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1.0 gram of 1,2,3,4,8,10,11,12,13,17-decahydroheptacen-6,15-dione and 1,2,3,4,10,11,12,13-octahydroheptacen-6,8(15H,17H)-dione and 20 mL of 2-methoxyethyl ether was stirred and flushed with nitrogen for 15 minutes. To this was added 0.766 grams of sodium borohydride. The resulting mixture was stirred overnight at room temperature. To the mixture was added 7.2 mL of methanol and stirring was continued for 30 minutes. To the resulting mixture was added 0.2 grams of sodium borohydride, and stirring was continued at room temperature for 5 hours. The resulting mixture was heated to 60° C. for one hour. To the mixture was added 11.4 mL of glacial acetic acid and 7.3 mL of concentrated hydrochloric acid. The resulting mixture was heated at 60° C. for one hour. To this mixture was added 20 mL of water and the resulting solid was collected by filtration. The solid was washed with water followed by acetone followed by tetrahydrofuran and dried to give 1,2,3,4,10,11,12,13-octahydroheptacene.

Workup

  1. customflushed with nitrogen for 15 minutes
  2. additionTo this was added 0.766 grams of sodium borohydride
  3. stirringThe resulting mixture was stirred overnight at room temperature
  4. additionTo the mixture was added 7.2 mL of methanol
  5. stirringstirring
  6. additionTo the resulting mixture was added 0.2 grams of sodium borohydride
  7. stirringstirring
  8. waitwas continued at room temperature for 5 hours
  9. additionTo the mixture was added 11.4 mL of glacial acetic acid and 7.3 mL of concentrated hydrochloric acid
  10. temperatureThe resulting mixture was heated at 60° C. for one hour
  11. additionTo this mixture was added 20 mL of water
  12. filtrationthe resulting solid was collected by filtration
  13. washThe solid was washed with water
  14. customdried

Sources & evidence

ORD record
ord-c4015d21af084bebbd3d5516081a424b
Source dataset
uspto-grants-2005_12
Patent number
US06974877B2

Reaction notes

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