Ethanethiol → HCID 15708214, compound

HRID 893115Notes

Reaction equation

HRID 893115 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C:12](=[CH2:18])[C:13]([O:15]CC)=[O:14])=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[CH2:25]([SH:27])[CH3:26]>C(OCC)(=O)C>[CH2:25]([S:27][CH2:18][CH:12]([CH2:11][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=[CH:2][CH:3]=1)[C:13]([OH:15])=[O:14])[CH3:26]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 22418871HCID 22418871, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15708214HCID 15708214, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

597 mg of ethyl 2-(4-quinolylmethyl)acrylate was dissolved in 3 ml of ethylmercaptan. Then, 50 mg of potassium tert-butoxide was added thereto, and the mixture was stirred at room temperature for two hours. Then, the reaction solution was diluted with 60 ml of ethyl acetate and washed with 40 ml of water and then with 40 ml of a saturated sodium chloride aqueous solution. The organic layer was separated, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residual syrup was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/2) and dried to obtain 640 mg (yield: 85%) of the desired product as syrup.

Workup

  1. washwashed with 40 ml of water
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residual syrup was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/2)
  6. customdried

Sources & evidence

ORD record
ord-99a63eb89de54d82b71404bc9661e4f0
Source dataset
uspto-grants-1992_06
Patent number
US05122523

Reaction notes

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