Cyclopentanone, 2,3-epoxy- → HCID 20380382, compound

HRID 1448637Notes

Reaction equation

HRID 1448637 reaction equation
[O:1]1[CH:6]2[CH:2]1[C:3](=O)[CH2:4][CH2:5]2.[OH:8][C:9]([CH3:17])([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:10][SH:11]>C(OCC)C.C(N(CC)CC)C>[OH:8][C:9]([CH3:17])([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:10][S:11][C:2]1[C:6](=[O:1])[CH2:5][CH2:4][CH:3]=1

Participants

5

Reactant 2

HCID 242082Cyclopentanone, 2,3-epoxy-HCID 135068602-Methyl-1-sulfanylheptan-2-OL

Product 1

HCID 20380382HCID 20380382, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 3283Diethyl EtherSolvent

Procedure

2,3-Epoxycyclopentanone (1.47 g) and 2.0 g of 2-hydroxy-2-methylheptyl mercaptan were dissolved in 30 ml of diethyl ether, and 30 drops of triethylamine were added. They were reacted at room temperature for 2 hours. The solvent was distilled off from the reaction mixture to afford 4.01 g of a crude product. The crude product was chromatographed on a dry column with cyclohexane/ethyl acetate (=8/2) to afford 2.07 g of 2-(2-hydroxy-2-methylheptylthio)cyclopent-2-en-1-one in a yield of 69%. The product had the following characteristics.

Workup

  1. customThey were reacted at room temperature for 2 hours
  2. distillationThe solvent was distilled off from the reaction mixture
  3. customto afford 4.01 g of a crude product
  4. customThe crude product was chromatographed on a dry column with cyclohexane/ethyl acetate (=8/2)

Sources & evidence

ORD record
ord-aab05748b7c1459ca5f8285491ce019b
Source dataset
uspto-grants-1979_12
Patent number
US04180672

Reaction notes

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