Tetrahydrofuran → HCID 22719305, compound

HRID 1582023Notes

Reaction equation

HRID 1582023 reaction equation
[N+:1]([C:4]1[C:16]2[C:15]3[C:10](=[CH:11][C:12]([N+:20]([O-:22])=[O:21])=[CH:13][C:14]=3[N+:17]([O-:19])=[O:18])[C:9](=[O:23])[C:8]=2[CH:7]=[C:6]([C:24]([O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][OH:38])=[O:25])[CH:5]=1)([O-:3])=[O:2].[CH2:39](N(CC)CC)C.[CH2:46]1C[O:49][CH2:48][CH2:47]1>>[N+:1]([C:4]1[C:16]2[C:15]3[C:10](=[CH:11][C:12]([N+:20]([O-:22])=[O:21])=[CH:13][C:14]=3[N+:17]([O-:19])=[O:18])[C:9](=[O:23])[C:8]=2[CH:7]=[C:6]([C:24]([O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][O:38][C:48](=[O:49])[C:47]([CH3:46])=[CH2:39])=[O:25])[CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 22719308HCID 22719308, compound

Product 1

HCID 22719305HCID 22719305, compoundYield 51%

Conditions

Temperature
0 °C

Procedure

0.7 g (1.3 mmol) 22, 0.15 g (1.44 mmol) 19 and 0.5 g activated molecular sieves (4 Å) were added to dry THF (10 ml). After the mixture was cooled to 0° C., 0.15 g (1.44 mmol) triethylamine was added. Then it was allowed to reach room temperature and was stirred for three hours. Ammonium salts were filtered off, the THF was evaporated and the crude product was redissolved in chloroform. The solution was extracted three times with diluted potassium hydroxide solution, two times with water, one time with brine and was then dried over magnesium sulfate. After the chloroform was evaporated, the monomer was purified by column chromatography on silica gel using 50% ethyl acetate in hexanes as eluent. The evaporation of the solvent yielded 0.4 g (51%) of a viscous dark orange oil. Rf=0.37 (EtOAc/hexanes: 1/1). 1H NMR (CDCl3, 500 MHz, 20° C.): d 8.99 (s, 1H), 8.85 (m, 2H), 8.74 (s, 1H), 6.10 (s, 1H), 5.56 (s, 1H), 4.60 (m, 2H), 4.28 (m, 2H), 3.88 (m, 2H), 3.71 (m, 10H), 1.93 (s, 3H). 13C NMR (CDCl3, 125 MHz, 20° C.): d 184.9, 162.6, 149.6, 146.8, 138.5, 138.4, 137.6, 136.2, 136.1, 135.5, 131.7, 129.3, 125.7, 125.3, 122.6, 70.7, 69.1, 68.8, 65.7, 63.8, 18.3.

Workup

  1. customto reach room temperature
  2. filtrationAmmonium salts were filtered off
  3. customthe THF was evaporated
  4. dissolutionthe crude product was redissolved in chloroform
  5. extractionThe solution was extracted three times with diluted potassium hydroxide solution, two times with water, one time with brine
  6. dry with materialwas then dried over magnesium sulfate
  7. customAfter the chloroform was evaporated
  8. customthe monomer was purified by column chromatography on silica gel using 50% ethyl acetate in hexanes as eluent
  9. customThe evaporation of the solvent

Sources & evidence

ORD record
ord-cec922e9e9e84a29b4b15e97436ea6f7
Source dataset
uspto-grants-2004_05
Patent number
US06733883B2

Reaction notes

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