Ethylene Glycol → HCID 22174558, compound

HRID 1797284Notes

Reaction equation

HRID 1797284 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][O:5][CH2:6][CH2:7][O:8]CCO.[H-].[Na+].C(O)CO.BrC1C=CC=CC=1CBr>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][O:5][CH2:6][CH2:7][OH:8]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 24758Sodium hydrideHCID 769652-Bromobenzyl bromideHCID 9965373HCID 9965373, compound

Product 1

HCID 22174558HCID 22174558, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

The reaction and work up was conducted as described in the preparation of compound 415. Starting materials were NaH (60% in oil, 1.8 g, 44 mmol) in THF (160 mL), ethylenglycol (13.4 mL, 240 mmol), 2-bromo-benzyl bromide (10 g, 40 mmol) dissolved in 5 mL dry THF and tetrabutylammonium iodide (0.15 g, 0.4 mmol). The crude product was purified by flash chromatography using DCM/Acetone 30:1 as the eluent to afford the title compound as a pale yellow oil.

Workup

  1. customThe reaction and work
  2. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-d40dac316b6344079905830faf9baa24
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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