Ethylene Glycol → 2-(Benzo[b]thien-3-yloxy)ethanol

HRID 493309Notes

Reaction equation

HRID 493309 reaction equation
Br[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.O(C(C)(C)C)[K].[I-].[K+].[CH2:19]([OH:22])[CH2:20][OH:21]>[Cu]=O>[S:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:2]([O:21][CH2:20][CH2:19][OH:22])=[CH:3]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 4875Potassium IodideHCID 123250Benzo(b)thiophene, 3-bromo-HCID 178418922HCID 178418922, compound

Product 1

HCID 220364722-(Benzo[b]thien-3-yloxy)ethanolYield 60%

Reagents, catalysts & solvents 1

HCID 14829Copper oxideCatalyst

Conditions

Temperature
140 °C

Procedure

A mixture of 3-bromobenzothiophene (3.00 g, 14.1 mmol), KO-t-Bu (4.74 g, 42.2 mmol), copper (II) oxide (0.56 g, 7.0 mmol) and potassium iodide (2.34 g, 14.1 mmol) in ethylene glycol (10 mL) was stirred at 140° C. for 24 h. The reaction was quenched with water (100 mL) and filtered through a pad of Celite. The water phase was extracted with EtOAc (3×50 mL). The organic phase was treated with MgSO4 and silica, filtered through Celite and concentrated. The remaining oil was purified by column chromatography on silica using isohexane/EtOAc (6:4) as eluent. The product crystallized on standing to give 1.63 g (60%) of the title product: mp 55-56° C. Anal. (C10H10O2S) C, H.

Workup

  1. customThe reaction was quenched with water (100 mL)
  2. filtrationfiltered through a pad of Celite
  3. extractionThe water phase was extracted with EtOAc (3×50 mL)
  4. additionThe organic phase was treated with MgSO4 and silica
  5. filtrationfiltered through Celite
  6. concentrationconcentrated
  7. customThe remaining oil was purified by column chromatography on silica
  8. customThe product crystallized

Sources & evidence

ORD record
ord-5ce6790538204c71800c647064963206
Source dataset
uspto-grants-2009_05
Patent number
US07534794B2

Reaction notes

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