Dichloromethane → 3-benzylthiophene

HRID 256550Notes

Reaction equation

HRID 256550 reaction equation
O[C:2]1([CH:13]=[CH:12][CH:11]=[CH:10][CH2:9]1)[CH2:3][C:4]1[CH:8]=[CH:7][S:6][CH:5]=1.ClCCl>[Na]>[CH2:3]([C:4]1[CH:8]=[CH:7][S:6][CH:5]=1)[C:2]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 67883839HCID 67883839, compound

Product 1

HCID 104874713-benzylthiopheneYield 58.5%

Reagents, catalysts & solvents 1

HCID 5360545SodiumSolvent

Procedure

A solution containing P2I4 (3.42 g, 6 mmol) and 3-(1-hydroxybenzyl)thiophene (1.90 g, 10 mmol) in sodium-dried toluene (100 ml) was heated under nitrogen for one hour. The reaction mixture was cooled and then quenched with 10% aqueous sodium sulphite. The mixture was extracted with ether, and the combined organic phases were washed with water and brine then dried. Filtration and evaporation afforded a yellow oil, which on bulb-to-bulb distillation (110° C. at 0.05 mmHg) gave a pale-pink oil. Chromatography with dichloromethane gave 3-benzylthiophene as an oil (1.02 g, 53% yield); 1H nmr:delta 3.84 (2H,s), 7.0-7.2 (8H,m) ppm.

Workup

  1. temperaturewas heated under nitrogen for one hour
  2. temperatureThe reaction mixture was cooled
  3. customquenched with 10% aqueous sodium sulphite
  4. extractionThe mixture was extracted with ether
  5. washthe combined organic phases were washed with water and brine
  6. customthen dried
  7. filtrationFiltration and evaporation
  8. customafforded a yellow oil, which
  9. distillationon bulb-to-bulb distillation (110° C. at 0.05 mmHg)
  10. customgave a pale-pink oil

Sources & evidence

ORD record
ord-0885e3156d4045629ec7469a6e6d5deb
Source dataset
uspto-grants-1993_11
Patent number
US05258360

Reaction notes

Loading…