2-Chloroethanol → 2-{[2-(2-Pyridinyl)ethyl]thio}ethanol

HRID 2108137Notes

Reaction equation

HRID 2108137 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][SH:9].[OH-].[K+].Cl[CH2:13][CH2:14][OH:15].Cl>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][S:9][CH2:13][CH2:14][OH:15]

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 1509632-Pyridineethanethiol

Product 1

HCID 234225272-{[2-(2-Pyridinyl)ethyl]thio}ethanolYield 22.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Pyridineethanethiol (1.9 g) and potassium hydroxide (0.77 g) in methanol (15 ml) were stirred under nitrogen for 15 min. 2-Chloroethanol (1.10 g) was added and the solution stirred under nitrogen for 6 h. The mixture was acidified to pH5 with 2N hydrochloric acid and then left overnight. The methanol was evaporated in vacuo and the residue partitioned between water (150 ml) and diethyl ether (150 ml), separated and the aqueous phase re-extracted with diethyl ether (100 ml). The combined ethereal layers were dried and evaporated in vacuo to give an oil. Purification by FCC eluting with System G (98:2:1) gave the title compound (0.56 g) as a colourless oil. T.l.c. (diethyl ether) Rf 0.21

Workup

  1. waitleft overnight
  2. customThe methanol was evaporated in vacuo
  3. customthe residue partitioned between water (150 ml) and diethyl ether (150 ml)
  4. customseparated
  5. extractionthe aqueous phase re-extracted with diethyl ether (100 ml)
  6. customThe combined ethereal layers were dried
  7. customevaporated in vacuo
  8. customto give an oil
  9. customPurification by FCC
  10. washeluting with System G (98:2:1)

Sources & evidence

ORD record
ord-a307161e8c8247f284a3ea1321488677
Source dataset
uspto-grants-1990_06
Patent number
US04937268

Reaction notes

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