Chloroform → 3-Thiopheneethanol methanesulfonate

HRID 343977Notes

Reaction equation

HRID 343977 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][OH:8])=[CH:2]1.[CH3:9][S:10](Cl)(=[O:12])=[O:11].C(Cl)(Cl)Cl>N1C=CC=CC=1>[CH3:9][S:10]([O:8][CH2:7][CH2:6][C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 31297Methanesulfonyl chlorideHCID 83731Thiophene-3-ethanol

Product 1

HCID 144229343-Thiopheneethanol methanesulfonateYield 65%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 5.0 g (7.8×10-3 mol) of 2-(3-thienyl)-ethanol (Aldrich Chemical) in 10 ml of dry, freshly distilled pyridine was added 3.62 ml (1.2 equiv.) of methanesulfonyl chloride in 20 ml of pyridine at 5°-10° C. The addition was carried out gradually, over a period of about 15-20 min. The reaction mixture was stirred overnight at room temperature and was quenched by pouring into a separatory funnel containing water and ether. The layers were separated and the aqueous layer was extracted three times with ether. The combined organic extracts were extracted once with 10% hydrochloric acid, followed by water and drying over Na2SO4. Evaporation of the solvent afforded 5.3 g of a light brown oil (65% yield), and tlc (CHCl3) showed a single spot. Chromatographic purification on silica gel afforded a light yellow oil. Nmr (CDCl3, δ rel TMS) 2.9s, 3H; 3.1t, 2H; 4.4t, 2H; 7.0-7.4m, 3H. Ir (neat, ν cm-1) 3100w, 2930w, 2920w 1415w, 1355s, 1335s, 1245w, 1173s, 1080w, 1055w, 970s, 955s, 903m, 850m, 825w, 795s, 775s, 740w. MS, 206.0.

Workup

  1. additionThe addition
  2. customwas quenched
  3. additionby pouring into a separatory funnel
  4. additioncontaining water and ether
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted three times with ether
  7. extractionThe combined organic extracts were extracted once with 10% hydrochloric acid
  8. dry with materialdrying over Na2SO4
  9. customEvaporation of the solvent

Sources & evidence

ORD record
ord-7009de23668a4dbea7d61b6105c38d5d
Source dataset
uspto-grants-1999_01
Patent number
US05863981

Reaction notes

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