Sodium hydride → HCID 9943663, compound

HRID 1797286Notes

Reaction equation

HRID 1797286 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]OCCO.[H-].[Na+].[F:18][C:19]([F:24])([F:23])CCO.BrC1C=CC=CC=1CBr>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:18][C:19]([F:24])([F:23])[CH2:7][CH2:6][O:5][CH2:4][C:3]1[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=1[Br:1]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 769652-Bromobenzyl bromideHCID 1375123,3,3-Trifluoro-1-propanolHCID 9965373HCID 9965373, compound

Product 1

HCID 9943663HCID 9943663, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The reaction and work up was conducted as described in the preparation of compound 415. Starting materials were NaH (60% in oil, 0.08 g, 2 mmol) in dry THF (10 mL), 3,3,3-trifluoropropan-1-ol (0.23 g, 2 mmol), 2-bromo-benzylbromide (0.50 g, 2 mmol) and tetrabutylammonium iodide (0.74 g, 0.2 mmol). The crude product was purified by flash chromatography using EtOAc/petroleum ether 1 : 35 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-64156ce9accf47009b20e4764210341b
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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