Ethanethiol → HCID 15708214, compound

HRID 1720642Notes

Reaction equation

HRID 1720642 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-0f509fd956074c83953991f49e37ef9c
Source dataset
uspto-grants-1996_04
Patent number
US05506356

Reaction notes

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