Ethylene Glycol → 2-(3-Thienylmethoxy)ethanol

HRID 1464754Notes

Reaction equation

HRID 1464754 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[H-].[Na+].CN(C)C=O.Br[CH2:13][C:14]1[CH:18]=[CH:17][S:16][CH:15]=1>O1CCCC1>[S:16]1[CH:17]=[CH:18][C:14]([CH2:13][O:3][CH2:2][CH2:1][OH:4])=[CH:15]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 5207033-(Bromomethyl)thiophene

Product 1

HCID 199170562-(3-Thienylmethoxy)ethanolYield 101.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

621 mg of ethylene glycol was dissolved in 1 ml of tetrahydrofuran, and 88 mg of 60% oily sodium hydride and 0.5 ml of dimethylformamide were added. After the mixture was stirred at room temperature for 5 minutes, a tetrahydrofuran solution(1 ml) of 200 mg of 3-bromomethylthiophene was added. The mixture was stirred at 60 ° C. for 2 hours, and then the solvent was evaporated. The residue was worked up in a customary manner to give 181 mg of the captioned compound as a pale yellow oil.

Workup

  1. stirringThe mixture was stirred at 60 ° C. for 2 hours
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d34c7b13f01b45448a0bad9204234eef
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

Loading…