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Potassium Carbonate → HCID 23437305, compound

HRID 2120019
Notes
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Reaction equation

HRID 2120019 reaction equation
[OH:1][C:2]1[C:19]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][C:13]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[C:14]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:15]=3)[C:10]3[C:5](=[CH:6][C:7]([O:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])=[C:8]([O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:9]=3)[C:4]=2[CH:3]=1.Br[CH2:56][CH2:57][O:58][CH2:59][CH2:60][O:61][CH3:62].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[O:1]([C:2]1[C:19]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][C:13]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[C:14]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:15]=3)[C:10]3[C:5](=[CH:6][C:7]([O:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])=[C:8]([O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:9]=3)[C:4]=2[CH:3]=1)[CH2:56][CH2:57][O:58][CH2:59][CH2:60][O:61][CH3:62]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1235321-Bromo-3,6-dioxaheptaneHCID 15399808HCID 15399808, compound

Product 1

HCID 23437305HCID 23437305, compoundYield 14.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-hydroxy-3,6,7,10,11-pentahexyloxytriphenylene (0.37 g, 0.5 mmol), 1-bromo-2-(2-methoxyethoxy)ethane (0.37 g) and potassium carbonate (0.4 g, 3 mmol) in ethanol (10 ml) was heated under reflux for 72 hours. After which time, it was filtered, extracted with dichloromethane (25 ml), concentrated in vacuo, and the product isolated by column chromatography (silica gel eluting with ethyl acetate) and recrystallised from ethanol to give the title compound as a white solid (0.06 g, 14%, K→D 55.4° C., D→I 69.3° C.). Elemental Analysis: C, 74.95; H, 9.55. C53H82O8 requires: C, 75.14; H, 9.75. Mass Spectrum: m/z (FAB) 869 ([M+23]+, 100%); 846 (M+, 94.5%). 1H-NMR: δH (CDCl3) 0.93 (15H, t, J=6.7 Hz, O(CH2)5CH3), 1.10-1.70 (30H, m, OCH2CH2(CH2)3), 1.94 (10H, m, OCH2CH2), 3.41 (3H, s, OCH2CH2OCH2CH2CH3), 3.61 (2H, t, J=5.0 Hz, OCH2CH2OCH2CH2), 3.82 (2H, t, J=5.0 Hz, OCH2CH2OCH2), 4.00 (2H, t, J=5.0 Hz, OCH2CH2), 4.23 (10H, t, J=6.5 Hz, OCH2), 4.42 (2H, t, J=5.0 Hz, OCH2), 7.83 (5H, s, ArH), 7.90 (1H, s, ArH).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 72 hours
  3. filtrationAfter which time, it was filtered
  4. extractionextracted with dichloromethane (25 ml)
  5. concentrationconcentrated in vacuo
  6. customthe product isolated by column chromatography (silica gel eluting with ethyl acetate)
  7. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-18f76a9336f14e0fb23a0eb449120073
Source dataset
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06689290B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes