反应 #833521

ord-98a84b136f9f4205a831f4692a94dbfe

反应方程式

C1CCOC1
THF
CCCCCCCCCCOc1cc2c3cc(OCCCCCCCCCC)c(OCCCCCCCCCC)cc3c3c(OC)ccc(OC)c3c2cc1OCCCCCCCCCC
4a
CCCCCCCCCCOc1cc2c3cc(OCCCCCCCCCC)c(OCCCCCCCCCC)cc3c3c(OC)ccc(OC)c3c2cc1OCCCCCCCCCC
1,4-dimethoxy-6,7,10,11-tetrakis(decyloxy)triphenylene
CCCCCCCCCCOc1cc2c3c(c4cc(OCCCCCCCCCC)c(OCCCCCCCCCC)cc4c2cc1OCCCCCCCCCC)C(=O)C=CC3=O
5a
收率 80.0%
CCCCCCCCCCOc1cc2c3c(c4cc(OCCCCCCCCCC)c(OCCCCCCCCCC)cc4c2cc1OCCCCCCCCCC)C(=O)C=CC3=O
6,7,10,11-tetrakis(decyloxy)triphenylene-1,4-dione
收率 80.0%

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    洗涤washed with a saturated solution of NaHCO3 and water
  2. 2
    干燥The organic layer was dried with MgSO4
  3. 3
    其他the solvent removed under reduced pressure
  4. 4
    其他The crude product was purified by column chromatography on silica gel (1:1 CH2Cl2/hexane)

实验过程

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.).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07393503B2uspto-grants-2008_07