Triethylamine → HCID 19362537, compound

HRID 850258Notes

Reaction equation

HRID 850258 reaction equation
[OH:1][N:2]=[C:3]1[C:15]2[CH:14]=[CH:13][C:12]([O:16][CH3:17])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[C:7]([O:18][CH3:19])[CH:8]=2.C(N(CC)CC)C.[CH2:27]([C:39]1[CH:44]=[CH:43][C:42]([S:45](Cl)(=[O:47])=[O:46])=[CH:41][CH:40]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>C1COCC1>[CH2:27]([C:39]1[CH:40]=[CH:41][C:42]([S:45]([O:1][N:2]=[C:3]2[C:4]3[CH:5]=[CH:6][C:7]([O:18][CH3:19])=[CH:8][C:9]=3[C:10]3[C:15]2=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=3)(=[O:47])=[O:46])=[CH:43][CH:44]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1042154-Dodecylbenzenesulfonyl chlorideHCID 19362527HCID 19362527, compound

Product 1

HCID 19362537HCID 19362537, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As described under 11.3., 5.1 g (0.02 mol) of 9-hydroxyimino-3,6-dimethoxyfluorene are reacted at 0° C., in the presence of 3.0 g (0.03 mol) of triethylamine in 100 ml THF, with 5.6 g (0.022 mol) of 4-dodecylbenzenesulfonyl chloride. The crude product obtained after isolation is purified by flash chromatography on silica gel (eluant: petroleum ether/ethyl acetate 4:1). 5.8 g (51.3%) of 9-(4-dodecyl-phenylsulfonyloxyimino)-3,6-dimethoxyfluorene are obtained in the form of a viscous yellow oil. The UV spectrum (acetonitrile) of the substance shows absorption bands with a maximum at 315 nm (ε=21100) that extend to 443 nm. Elemental analysis: C33H41NO5S (563.76)

Workup

  1. customThe crude product obtained after isolation
  2. customis purified by flash chromatography on silica gel (eluant: petroleum ether/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-c6095bf903ac480182938afd329611c7
Source dataset
uspto-grants-2000_01
Patent number
US06017675

Reaction notes

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