Pyridine → HCID 54045408, compound

HRID 865992Notes

Reaction equation

HRID 865992 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 10% hydrochloric acid, followed by extraction with water and drying with Na2SO4. Evaporation 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; 4.22 t, 2H; 7.07-6.80 d, 2H; 7.37-7.13, H.

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 10% hydrochloric acid
  8. extractionfollowed by extraction with water
  9. dry with materialdrying with Na2SO4
  10. customEvaporation of the solvent

Sources & evidence

ORD record
ord-4722a144980741efa0394f00b84c2b5e
Source dataset
uspto-grants-1996_10
Patent number
US05569708

Reaction notes

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