Sodium hydride → Ethyl 6-[p-[5-(2-pyridyloxy)pentyloxy)phenoxy]-2,2-dimethylhexanoate

HRID 476980Notes

Reaction equation

HRID 476980 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:35]=[CH:34][C:20]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([CH3:33])([CH3:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:19][CH:18]=1>CN(C)C=O>[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[O:3][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:35]=[CH:34][C:20]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([CH3:33])([CH3:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 14851566Ethyl 6-[p-(5-bromopentyloxy)phenoxy]-2,2-dimethylhexanoateHCID 178516071HCID 178516071, compound

Product 1

HCID 14327301Ethyl 6-[p-[5-(2-pyridyloxy)pentyloxy)phenoxy]-2,2-dimethylhexanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into 5 ml of dry dimethylformamide containing 150 mg of sodium hydride (60% suspension in mineral oil) was added 292 mg of 2-hydroxypyridine. After stirring the mixture at room temperature for 15 minutes, 1.2 g of ethyl 6-[p-(5-bromopentyloxy)phenoxy]-2,2-dimethylhexanoate was added thereto. The mixture was stirred at room temperature for 12 hours, and thereafter the solvent was removed from the reaction solution under reduced pressure. The remaining oily substance was dissolved in chloroform, washed with water, and then dried over anhydrous magnesium sulfate. After drying, the solvent was distilled off under reduced pressure. The remaining oily substance was subjected to silica gel column chromatography and the product was eluted out using as an eluent chloroform-methanol (99:1). The solvent was distilled off from the eluate under reduced pressure to give the desired ethyl 6-[p-[5-(2-pyridyloxy)pentyloxy)phenoxy]-2,2-dimethylhexanoate as an oily substance (495 mg).

Workup

  1. stirringThe mixture was stirred at room temperature for 12 hours
  2. customthe solvent was removed from the reaction solution under reduced pressure
  3. dissolutionThe remaining oily substance was dissolved in chloroform
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter drying
  7. distillationthe solvent was distilled off under reduced pressure
  8. washthe product was eluted out
  9. distillationThe solvent was distilled off from the eluate under reduced pressure

Sources & evidence

ORD record
ord-996cb42976d94b9fb8f7fd96306de3a6
Source dataset
uspto-grants-1989_12
Patent number
US04886818

Reaction notes

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