Hydrochloric Acid → HCID 23468930, compound

HRID 128311Notes

Reaction equation

HRID 128311 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:11]([Br:12])=[CH:10][C:9]([CH:13]([CH2:17][CH2:18][OH:19])[CH2:14][CH2:15][OH:16])=[CH:8][C:5]=2[C:6]=1[CH3:7].[CH3:20][S:21](Cl)(=[O:23])=[O:22].Cl>N1C=CC=CC=1>[CH3:20][S:21]([O:19][CH2:18][CH2:17][CH:13]([C:9]1[CH:10]=[C:11]([Br:12])[C:4]2[O:3][C:2]([CH3:1])=[C:6]([CH3:7])[C:5]=2[CH:8]=1)[CH2:14][CH2:15][O:16][S:21]([CH3:20])(=[O:23])=[O:22])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 23468795HCID 23468795, compound

Product 1

HCID 23468930HCID 23468930, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

16.4 g (0.05 mol) of 3-(2,3-dimethyl-7-bromo-5-benzofuranyl)-1,5-pentanediol are dissolved in 200 ml of pyridine. The solution is cooled to -8° to -10° and 8.5 ml (=12.6 g, 0.11 mol) of methanesulfonyl chloride are added dropwise at this temperature in the course of 30 minutes. The reaction mixture is allowed to react at -8° to -10° for 11/2 hours and is then poured onto 500 g of ice and the pH value is adjusted to about 1 by adding 5 N hydrochloric acid. This acid mixture is extracted 3 times with methylene chloride and the extracts are washed twice with 2 N hydrochloric acid and 3 times with water. The combined extracts are dried over sodium sulfate and the solvent is evaporated off under a waterpump vacuum. A crude product which crystallises spontaneously and has a melting point of 154°-156° is thereby obtained. Recrystallisation from methylene chloride/hexane gives 3-(2,3-dimethyl-7-bromo-5-benzofuranyl)-1,5-pentanediyl dimethanesulfonate as white crystals of melting point 158°-159°.

Workup

  1. temperatureThe solution is cooled to -8° to -10°
  2. customto react at -8° to -10° for 11/2 hours
  3. extractionThis acid mixture is extracted 3 times with methylene chloride
  4. washthe extracts are washed twice with 2 N hydrochloric acid and 3 times with water
  5. dry with materialThe combined extracts are dried over sodium sulfate
  6. customthe solvent is evaporated off under a waterpump vacuum
  7. customA crude product which crystallises spontaneously
  8. customis thereby obtained
  9. customRecrystallisation from methylene chloride/hexane

Sources & evidence

ORD record
ord-bbb92434d6344fb7b980c4dbe347a750
Source dataset
uspto-grants-1981_03
Patent number
US04259338

Reaction notes

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