Sodium hydride → Ethyl 4-(3-pentyloxyphenoxy)butyrate

HRID 439754Notes

Reaction equation

HRID 439754 reaction equation
[H-].[Na+].[CH2:3]([O:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1)[CH2:4][CH2:5][CH2:6][CH3:7].Br[CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C)C=O>[CH2:3]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[O:15][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 156922293-(Pentyloxy)phenol

Product 1

HCID 22407863Ethyl 4-(3-pentyloxyphenoxy)butyrate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 7.3 g of 60% NaH in 190 ml of anhydrous dimethylformamide is cooled in an ice bath. To this mixture is added 22.0 g of 3-pentyloxyphenol dissolved in 50 ml of anhydrous dimethylformamide. This mixture is then stirred at room temperature for 45 minutes; 23.2 ml of ethyl 4-bromobutyrate are added; and the resultant mixture is stirred at 60° C. for 17 hours. The solvent is removed under vacuum and the residue worked up as above. The residue is flash chromatographed on normal phase silica gel using a gradient from hexane to a 4:1 ratio of hexane:ether to yield ethyl 4-(3-pentyloxyphenoxy)butyrate as a clear oil.

Workup

  1. temperatureis cooled in an ice bath
  2. customThe solvent is removed under vacuum
  3. customchromatographed on normal phase silica gel using a gradient from hexane to a 4:1 ratio of hexane

Sources & evidence

ORD record
ord-22676dae95144dcb8920a1d205ec03c3
Source dataset
uspto-grants-1996_05
Patent number
US05516767

Reaction notes

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