6,13-Pentacenequinone → HCID 178521537, compound

HRID 1895565

Reaction equation

HRID 1895565 reaction equation
[CH:1]1[C:22]2[C:5](=[CH:6][C:7]3[C:8](=[O:24])[C:9]4[C:18]([C:19](=[O:23])[C:20]=3[CH:21]=2)=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=4)[CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[OH:23][C@H:19]1[C:18]2[C:9](=[CH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[C@H:8]([OH:24])[C:7]2[CH:6]=[C:5]3[C:22]([CH:1]=[CH:2][CH:3]=[CH:4]3)=[CH:21][C:20]1=2

Participants

4

Reactant 2

HCID 764156,13-PentacenequinoneHCID 4311764Sodium borohydride

Product 1

HCID 178521537HCID 178521537, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 6,13-pentacenequinone (1.0 g, 3.24 mmol) in dry MeOH (40 mL) at 0° C. under an argon atmosphere was slowly added NaBH4 (1.22 g, 32.46 mmol). The reaction mixture was stirred at 0° C. for 0.5 h and at RT for 1 h, and then quenched with H2O at 0° C. The resulting mixture was filtered and washed with H2O. The resulting solid was taken up in CHCl3, then filtered and washed with CHCl3, and dried in vacuo to give product as an off-white solid (0.92 g, 91%): mp 235° C. 1H NMR (500 MHz, DMSO-d6): δ 8.12 (s, 4H), 7.95 (m, 4H), 7.48 (m, 4H), 6.63 (s, 2H), 5.81 (s, 2H). 13C NMR (125.68 MHz, DMSO-d6): δ 138.19, 131.67, 127.47, 125.44, 120.91, 66.98. LDI-MS m/z: 312 [M+], 296 [M+-OH], 280 [M+-2(OH)].

Workup

  1. customquenched with H2O at 0° C
  2. filtrationThe resulting mixture was filtered
  3. washwashed with H2O
  4. filtrationfiltered
  5. washwashed with CHCl3
  6. customdried in vacuo

Sources & evidence

ORD record
ord-be057a0002e1450a959314afc1d4a9d8
Source dataset
uspto-grants-2013_08
Patent number
US08513466B2

Linked notes

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