Dimethylformamide → HCID 19917015, compound

HRID 1464775Notes

Reaction equation

HRID 1464775 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=2)[O:9][CH2:10][CH2:11][OH:12])=[CH:2]1.[H-].[Na+].CN(C)C=O.Br[CH:24]([CH3:29])[C:25]([O:27][CH3:28])=[O:26]>O1CCCC1.O.C(OCC)C>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=2)[O:9][CH2:10][CH2:11][O:12][CH:24]([CH3:29])[C:25]([O:27][CH3:28])=[O:26])=[CH:2]1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 95576Methyl 2-bromopropionateHCID 19916949HCID 19916949, compound

Product 1

HCID 19917015HCID 19917015, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.22 g of 2-[3-(3-thienyl)phenoxy]ethanol was dissolved in 7 ml of tetrahydrofuran, and 48 mg of 60% oily sodium hydride was added. After the mixture was stirred at room temperature for 20 minutes, a dimethylformamide solution (5 ml) of 0.14 ml of methyl α-bromopropionate was added. The mixture was stirred at room temperature for 1.5 hours, and then ethyl ether and water were added. The organic layer separated was worked up in a customary manner, and the product was purified by silica gel column chromatography [hexane / ethyl acetate=10 / 1] to give 0.22 g of methyl 2-[2-[3-(3-thienyl)phenoxy] ethoxy]propionate as a colorless oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 1.5 hours
  2. customThe organic layer separated
  3. customthe product was purified by silica gel column chromatography [hexane / ethyl acetate=10 / 1]

Sources & evidence

ORD record
ord-462b8a6ceb3944199cf854e1b6a2c2aa
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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