Water → HCID 22768841, compound

HRID 1764657Notes

Reaction equation

HRID 1764657 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.C(Cl)Cl.O>CCOCC>[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[O:8][C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:26])=[O:25])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 74014-Methoxybenzenesulfonyl chlorideHCID 35179362-Phenyl-benzofuran

Product 1

HCID 22768841HCID 22768841, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3.9 g.(0.02 mol.) of 2-phenylbenzofuran and 6.2 g. (0.03 mol.) of 4-methoxybenzenesulfonyl chloride in 50 ml. of methylene chloride was added 3.5 ml. (7.83 g., 0.03 mol.) of stannic chloride. The reaction mixture was stirred at ambient temperature for about 12 hours then poured into 150 ml. of water. The layers were separated and the organic phase was extracted once with 10% aqueous sodium bicarbonate solution, three times with water and once with a saturated sodium chloride solution, dried (MgSO4) and evaporated to dryness to give a residue. Ether (ca. 35 ml.) was added to the residue and it was refluxed for 1 hour then filtered. The solid collected was recrystallized from benzene-hexane then chromatographed on a silica gel "dry column" with methylene chloride as eluant to give 3-(4-methoxyphenylsulfonyl)-2-phenylbenzofuran, m.p. 146°-148°.

Workup

  1. additionthen poured into 150 ml
  2. customThe layers were separated
  3. extractionthe organic phase was extracted once with 10% aqueous sodium bicarbonate solution, three times with water and once with a saturated sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customto give a residue
  7. temperaturewas refluxed for 1 hour
  8. filtrationthen filtered
  9. customThe solid collected
  10. customwas recrystallized from benzene-hexane
  11. customthen chromatographed on a silica gel "
  12. dry with materialdry column" with methylene chloride as eluant

Sources & evidence

ORD record
ord-808d2156cb824935a6d32f9f809567a6
Source dataset
uspto-grants-1978_09
Patent number
US04117128

Reaction notes

Loading…