Tetrahydrofuran → 6,7,10,11-Tetrakis(decyloxy)triphenylene-1,4-dione

HRID 1257950Notes

Reaction equation

HRID 1257950 reaction equation
C1COCC1.C[O:7][C:8]1[C:25]2[C:24]3[C:19](=[CH:20][C:21]([O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[C:22]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:23]=3)[C:18]3[C:13](=[CH:14][C:15]([O:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH3:69])=[C:16]([O:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[CH:17]=3)[C:12]=2[C:11]([O:70]C)=[CH:10][CH:9]=1>CCOCC>[CH2:27]([O:26][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][C:21]=1[O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[C:18]1[C:13](=[CH:14][C:15]([O:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH3:69])=[C:16]([O:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[CH:17]=1)[C:12]1[C:11](=[O:70])[CH:10]=[CH:9][C:8](=[O:7])[C:25]2=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 536909211,4-Dimethoxy-6,7,10,11-tetrakis(decyloxy)triphenylene

Product 1

HCID 537372916,7,10,11-Tetrakis(decyloxy)triphenylene-1,4-dioneYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

An aqueous solution (1 mL) of (NH4)2Ce(NO3)6 (0.035 g, 0.064 mmol) was added dropwise to a THF solution (5 mL) of 4a (0.029 g, 0.032 mmol). The reaction mixture immediately turned deep red. After 6 h the reaction mixture was poured into ether and washed with a saturated solution of NaHCO3 and water. The organic layer was dried with MgSO4 and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel (1:1 CH2Cl2/hexane) to afford 5a as a deep red solid in 80% yield (mp 86-87° C.).

Workup

  1. washwashed with a saturated solution of NaHCO3 and water
  2. dry with materialThe organic layer was dried with MgSO4
  3. customthe solvent removed under reduced pressure
  4. customThe crude product was purified by column chromatography on silica gel (1:1 CH2Cl2/hexane)

Sources & evidence

ORD record
ord-e1950e4b424c4321b1966d2c20e132ec
Source dataset
uspto-grants-2013_06
Patent number
US08465678B2

Reaction notes

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