Pyridine → HCID 54045408, compound

HRID 442996Notes

Reaction equation

HRID 442996 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][CH2:8][CH2:9][OH:10])=[CH:2]1.N1C=CC=CC=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)(Cl)Cl>[CH3:17][S:18]([O:10][CH2:9][CH2:8][CH2:7][CH2:6][C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 54222621HCID 54222621, compound

Product 1

HCID 54045408HCID 54045408, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1.05 g (6.7×10-3 mol) of 4-(3-thienyl)-butanol in 25 ml of dry, freshly distilled pyridine was added 0.85 g (1.1 equiv.) of methane-sulfonyl chloride at 25° C. The addition was gradual and carried out over a several minute period. The reaction mixture was stirred for 6 hr at room temperature and quenched by pouring into a separtory funnel containing water-HCl and ether. The layers were separated and the aqueous layer was extracted once with 10L hydrochloric acid, followed by extraction with water and drying with Na2SO4Evaporation of the solvent afforded 1.51 g of a light brown oil (95% yield), tlc (CHCl3) showed a single spot. El. Anal. Calcd. for C9H14O3S2 : C, 46.13; H, 6.02; S, 27.36. Found: C, 45.92; H, 5.94: S, 27.15. Nmr (CDCl3, δ rel TMS) 2.0-1.5 brs, 4H; 2.67 brt, 2H; 2.97s, 3H; 4.22t, 2H; 7.07-6.80d, 2H; 7.37-7.13, lH.

Workup

  1. additionThe addition
  2. waitcarried out over a several minute period
  3. customquenched
  4. additionby pouring into a separtory funnel
  5. additioncontaining water-HCl and ether
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted once with 10L hydrochloric acid
  8. extractionfollowed by extraction with water
  9. customdrying with Na2SO4Evaporation of the solvent

Sources & evidence

ORD record
ord-23960cd43015427abbb9ab36ab68ecd4
Source dataset
uspto-grants-1999_04
Patent number
US05891968

Reaction notes

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