Hydrogen Sulfide → HCID 13176139, compound

HRID 978622Notes

Reaction equation

HRID 978622 reaction equation
C(N(CC)CC)C.[CH2:8]([CH:13]1[C:17](O)([CH3:18])[CH:16]=[CH:15][C:14]1=[O:20])[CH2:9][CH2:10][CH2:11][CH3:12].[SH2:21]>C1(C)C=CC=CC=1>[CH2:8]([C:13]1[C:14](=[O:20])[CH2:15][CH:16]([SH:21])[C:17]=1[CH3:18])[CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 13137234HCID 13137234, compound

Product 1

HCID 13176139HCID 13176139, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into the same flask as used in Example 1, triethylamine (5 g), 2-n-pentyl-3-hydroxy-3-methyl-4-cyclopentenone (18.2 g) and toluene (30 g) were charged, and hydrogen sulfide (8 g) was introduced into the mixture at a temperature of 15° to 30° C. Thereafter, the reaction mixture was stirred at a temperature of 50° to 70° C. for 4 hours. After completion of the reaction, the mixture was washed with an acid and water in order. The organic layer was separated and concentrated to obtain 2-n-pentyl-3-methyl-4-mercapto-2-cyclopentenone (18.0 g). Yield, 91%. nD20 1.5212.

Workup

  1. additionwere charged
  2. customAfter completion of the reaction
  3. washthe mixture was washed with an acid and water in order
  4. customThe organic layer was separated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d84c93a4d93d4811b0cc5ff1b3c5e314
Source dataset
uspto-grants-1987_05
Patent number
US04665174

Reaction notes

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