Water → HCID 20148613, compound

HRID 569155Notes

Reaction equation

HRID 569155 reaction equation
[C:1]([O:4][CH2:5][CH3:6])(=O)[CH3:2].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][C:14]2[CH:19]=CC(/C=C/CSCCO)=[CH:16][CH:15]=2)[CH:8]=1.[OH2:27]>>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][C:14]2[CH:15]=[CH:16][C:1]([O:4][CH2:5][CH2:6][OH:27])=[CH:2][CH:19]=2)[CH:8]=1

Participants

4

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 15594573HCID 15594573, compound

Product 1

HCID 20148613HCID 20148613, compoundYield 89.5%

Procedure

In 3 ml of ethanol was dissolved 310 mg of potassium hydroxide, and 0.37 ml of mercaptoethanol was added to the resulting solution. To this solution was dropwise added the N,N-dimethylformamide solution obtained in (1) above with ice-cooling, and the resulting mixture was subjected to reaction at room temperature for 30 minutes. Subsequently, 30 ml of ethyl acetate and 20 ml of water were added to the reaction mixture, and the organic layer was separated, washed with three 20-ml portions of water, thereafter washed with 20 ml of a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 340 mg (yield 89.5%) of colorless crystals of (E)-2-[3-[4-(pyridin-3-ylmethyl)phenyl]allylthio]ethanol having a melting point of 73°-74° C.

Workup

  1. temperaturecooling
  2. customthe resulting mixture was subjected to reaction at room temperature for 30 minutes
  3. customthe organic layer was separated
  4. washwashed with three 20-ml portions of water
  5. washwashed with 20 ml of a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-6903b1ea27c3405bbcb516751ed830b4
Source dataset
uspto-grants-1988_03
Patent number
US04731370

Reaction notes

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