2-Dimethylaminopyridine → 2-[4-(4-Allyloxybutyloxy)benzoyloxy]-7-(4-octyloxybenzoyloxy)-9-methylfluorene

HRID 130271Notes

Reaction equation

HRID 130271 reaction equation
CN(C1C=CC=CN=1)C.Cl.C(N=C=NCCCN(C)C)C.[CH2:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([OH:37])=[O:36])=[CH:33][CH:32]=1)[CH:23]=[CH2:24].[CH2:40]([O:48][C:49]1[CH:72]=[CH:71][C:52]([C:53]([O:55][C:56]2[CH:68]=[CH:67][C:66]3[C:65]4[C:60](=[CH:61][C:62](O)=[CH:63][CH:64]=4)[CH:59]([CH3:70])[C:58]=3[CH:57]=2)=[O:54])=[CH:51][CH:50]=1)[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]>O.C(Cl)Cl>[CH2:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([O:37][C:62]2[CH:63]=[CH:64][C:65]3[C:66]4[C:58](=[CH:57][C:56]([O:55][C:53](=[O:54])[C:52]5[CH:51]=[CH:50][C:49]([O:48][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[CH:72][CH:71]=5)=[CH:68][CH:67]=4)[CH:59]([CH3:70])[C:60]=3[CH:61]=2)=[O:36])=[CH:33][CH:32]=1)[CH:23]=[CH2:24]

Participants

7

Reactant 4

HCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219606264-(4-Allyloxybutyloxy)benzoic acidHCID 585869377-Hydroxy-9-methyl-9H-fluoren-2-YL 4-(octyloxy)benzoate

Product 1

HCID 585868702-[4-(4-Allyloxybutyloxy)benzoyloxy]-7-(4-octyloxybenzoyloxy)-9-methylfluoreneYield 22%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

Dimethylaminopyridine 0.01 g and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride 0.8 g were added to a methylene chloride (50 ml) solution of 4-(4-allyloxybutyloxy)benzoic acid 0.84 g and 2-(4-octyloxybenzoyloxy)-7-hydroxy-9-methylfluorene (J1) 1.5 g while maintaining 5° C., and the mixture was further stirred at room temperature for 12 hours. Water 50 ml was added thereto, and the resulting organic layer was dried on anhydrous magnesium sulfate. A residue obtained by distilling the solvent off was refined by silica gel column chromatography to obtain 0.5 g of 2-[4-(4-allyloxybutyloxy)benzoyloxy]-7-(4-octyloxybenzoyloxy)-9-methylfluorene (J2).

Workup

  1. dry with materialthe resulting organic layer was dried on anhydrous magnesium sulfate
  2. customA residue obtained
  3. distillationby distilling the solvent

Sources & evidence

ORD record
ord-ae7a3c702cd44b77afbb4cee5dd6fb4f
Source dataset
uspto-grants-2008_06
Patent number
US07381350B2

Reaction notes

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