3-Phenylpropane-1-thiol → HCID 20380346, compound

HRID 1448636Notes

Reaction equation

HRID 1448636 reaction equation
[O:1]1[CH:6]2[CH:2]1[C:3](=O)[CH2:4][CH2:5]2.[C:8]1([CH2:14][CH2:15][CH2:16][SH:17])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(OCC)C.C(N(CC)CC)C>[C:8]1([CH2:14][CH2:15][CH2:16][S:17][C:2]2[C:6](=[O:1])[CH2:5][CH2:4][CH:3]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 905963-Phenylpropane-1-thiolHCID 242082Cyclopentanone, 2,3-epoxy-

Product 1

HCID 20380346HCID 20380346, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 3283Diethyl EtherSolvent

Procedure

2,3-Epoxycyclopentanone (1.0 g) and 1.06 g of 3-phenylpropyl mercaptan were dissolved in 20 ml of diethyl ether, and 20 drops of triethylamine were added. They were reacted at room temperature for 2 hours. After the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. The residue (1.50 g) was chromatographed on a dry column with cyclohexane/ethyl acetate (=8/2) to afford 1.03 g of 2-(3-phenylpropylthio)cyclopent-2-en-1-one in a yield of 64%. The product had the following characteristics.

Workup

  1. customThey were reacted at room temperature for 2 hours
  2. customAfter the reaction
  3. distillationthe solvent was distilled off from the reaction mixture under reduced pressure
  4. customThe residue (1.50 g) was chromatographed on a dry column with cyclohexane/ethyl acetate (=8/2)

Sources & evidence

ORD record
ord-b3b01b20ca894b0fa8de58edf1c1b37a
Source dataset
uspto-grants-1979_12
Patent number
US04180672

Reaction notes

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