Ethylene Glycol → 2-(Thiophen-3-yloxy)-ethanol

HRID 981783Notes

Reaction equation

HRID 981783 reaction equation
[Na].[I-].[K+].Br[C:5]1[CH:9]=[CH:8][S:7][CH:6]=1.[CH2:10]([OH:13])[CH2:11][OH:12]>[Cu]=O>[OH:12][CH2:11][CH2:10][O:13][C:5]1[CH:9]=[CH:8][S:7][CH:6]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 4875Potassium IodideHCID 133833-BromothiopheneHCID 5360545Sodium

Product 1

HCID 220362782-(Thiophen-3-yloxy)-ethanol

Reagents, catalysts & solvents 1

HCID 14829Copper oxideCatalyst

Procedure

Using the same reaction conditions as those of Example 7, sodium (2.0 g) in ethylene glycol (125 ml), copper (II) oxide (1.25 g) and potassium iodide (0.05 g) were reacted with 3-bromothiophene (5.0 g, 0.031 mol). Chromatography of the crude product on a silica column eluted initially with dichloromethane, then with a mixture of dichloromethane/methanol (95:5) yielded 3-(hydroxyethoxy)thiophene, as a white solid (1.9 g, 43%). M.p. 38°-39° C. (Found: C, 49.2; H, 5.3; S, 21.9. Calculated for C6H8O2S: C, 50.0; H, 5.6; S, 22.3%); EI m/e Intensity (%): 144 (100, M+), 100 (47, C4H4OS), 45 (17, C2H5O); δH(CDCl3) 6.10-7.11 (3H, m), 4.16 (2H, m), 3.84 (2H, m); δC(CDCl3): 60.8, 71.4, 97.7, 119.4, 124.8, 157.4 ppm.

Workup

  1. washChromatography of the crude product on a silica column eluted initially with dichloromethane
  2. additionwith a mixture of dichloromethane/methanol (95:5)

Sources & evidence

ORD record
ord-0eeba993832845ff8e7b436cffbf0dc8
Source dataset
uspto-grants-1991_02
Patent number
US04992559

Reaction notes

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