Water → HCID 18765879, compound

HRID 481003Notes

Reaction equation

HRID 481003 reaction equation
[H-].[Na+].[C:3]([NH:22][CH2:23][CH2:24][CH2:25][OH:26])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:27][CH2:28][C:29]1[C:30]([CH2:35]Br)=[CH:31][CH:32]=[CH:33][CH:34]=1.O>C1COCC1>[Br:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][O:26][CH2:25][CH2:24][CH2:23][NH:22][C:3]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 66665o-Bis(bromomethyl)benzeneHCID 31113793-(Tritylamino)propan-1-ol

Product 1

HCID 18765879HCID 18765879, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of NaH (909 mg/22.7 mmol) in THF (50 ml) was added 3-(tritylamino)-1-propanol, and the solution was stirred at reflux temperature for 2 hours. To the solution was added α,α′-dibromo-o-xylene, and the solution was stirred at reflux temperature for 16 hours. After cooling, the mixture was poured into water. The whole was extracted with ethyl acetate (100 ml×2). The combined organic layer was washed with brine (30 ml), dried over magnesium sulfate, filtered and concentrated. The residue was purified by column chromatography (SiO2, 200-350 mesh/hexane:ethyl acetate=100:0-20:1) to afford a yellow oil (4.84 g/51%).

Workup

  1. temperatureat reflux temperature for 2 hours
  2. stirringthe solution was stirred
  3. temperatureat reflux temperature for 16 hours
  4. temperatureAfter cooling
  5. extractionThe whole was extracted with ethyl acetate (100 ml×2)
  6. washThe combined organic layer was washed with brine (30 ml)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by column chromatography (SiO2, 200-350 mesh/hexane:ethyl acetate=100:0-20:1)
  11. customto afford a yellow oil (4.84 g/51%)

Sources & evidence

ORD record
ord-2f44e1db23cd43e3b97a77e873905bb6
Source dataset
uspto-grants-2003_11
Patent number
US06653313B2

Reaction notes

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