Sodium hydride → HCID 19825421, compound

HRID 2249284Notes

Reaction equation

HRID 2249284 reaction equation
[H-].[Na+].[CH2:3]([OH:14])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1.[Cl-].[NH4+]>CN(C)C=O>[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][O:14][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:20][C:19]2[CH:22]=[CH:23][C:16]([Br:15])=[CH:17][CH:18]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 371531,10-DecanediolHCID 685274-Bromobenzyl bromide

Product 1

HCID 19825421HCID 19825421, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 851 mg (21.3 mmol) of sodium hydride contained at 60% in mineral oil in dry dimethylformamide (60 ml) was added 1.21 g (6.94 mmol) of 1,10-decanediol in an atmosphere of argon, and the mixture was allowed to react at 40°-50° C. for 30 min. Then, 4.23 g (16.9 mmol) of 4-bromobenzyl bromide was added to the solution, and the mixture was reacted at room temperature for 18 hours. To the solution at 0° C. was added a saturated aqueous solution of ammonium chloride followed by extraction with ethyl acetate. The organic layer was washed with water and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography for separation and purification. Elution with dichloromethane-hexane (1:1) yielded 3.09 g (6.04 mmol) of 1,14-bis(4-bromophenyl)-2,13-dioxatetradecane.

Workup

  1. customto react at 40°-50° C. for 30 min
  2. customthe mixture was reacted at room temperature for 18 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. concentrationconcentrated under reduced pressure
  6. customThe residue thus obtained
  7. customwas subjected to silica gel column chromatography for separation and purification
  8. washElution with dichloromethane-hexane (1:1)

Sources & evidence

ORD record
ord-f5f0f4ccf7514630b428097de06e0e9e
Source dataset
uspto-grants-1991_08
Patent number
US05043142

Reaction notes

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