2-Propanethiol → HCID 13176136, compound

HRID 978619Notes

Reaction equation

HRID 978619 reaction equation
[CH2:1]([CH:4]1[C:8](O)([CH3:9])[CH:7]=[CH:6][C:5]1=[O:11])[CH:2]=[CH2:3].[CH:12]([SH:15])([CH3:14])[CH3:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:1]([C:4]1[C:5](=[O:11])[CH2:6][CH:7]([S:15][CH:12]([CH3:14])[CH3:13])[C:8]=1[CH3:9])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 63642-PropanethiolHCID 8471TriethylamineHCID 128798724-Hydroxy-4-methyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-one

Product 1

HCID 13176136HCID 13176136, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into the same flask as used in Example 1, 2-allyl-3-hydroxy-3-methyl-4-cyclopentenone (15.2 g), isopropylmercaptan (20 g), triethylamine (1 g) and toluene (45 g) were charged, and the mixture was stirred under a nitrogen stream at a temperature of 40° to 70° C. for 5 hours. After completion of the reaction, the mixture was washed with an acid, an alkali and water in order. The organic layer was separated and concentrated to give 2-allyl-3-methyl-4-isopropylthio-2-cyclopentenone (20.2 g). Yield, 96.3%. The product was purified by silica gel chromatography using toluene-ethyl acetate (10:1 by volume). nD20 1.5196.

Workup

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

Sources & evidence

ORD record
ord-3ff18a44328b42f29a5fb72884056f0d
Source dataset
uspto-grants-1987_05
Patent number
US04665174

Reaction notes

Loading…