2-Mercaptoethanol → HCID 13176143, compound

HRID 978624Notes

Reaction equation

HRID 978624 reaction equation
[OH:1][CH2:2][CH2:3][SH:4].[H-].[Na+].[CH2:7]([CH:10]1[C:14](O)([CH3:15])[CH:13]=[CH:12][C:11]1=[O:17])[CH:8]=[CH2:9]>O1CCCC1>[CH2:7]([C:10]1[C:11](=[O:17])[CH2:12][CH:13]([S:4][CH2:3][CH2:2][OH:1])[C:14]=1[CH3:15])[CH:8]=[CH2:9]

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 24758Sodium hydrideHCID 128798724-Hydroxy-4-methyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-one

Product 1

HCID 13176143HCID 13176143, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into the same flask as used in Example 1, 2-hydroxyethylmercaptan (35 g) and tetrahydrofuran (10 g) were charged, and sodium hydride (0.6 g) was added thereto at a temperature of 10° to 20° C. At the same temperature, the reaction mixture was stirred for 1 hour. Thereafter, 2-allyl-3-hydroxy-3-methyl-4-cyclopentenone (15.2 g) was dropwise added thereto at a temperature of 15° to 30° C. for 1 hour, followed by stirring at the same temperature for 2 hours and at a temperature of 40° to 70° C. for 3 hours. After completion of the reaction, the mixture was treated in the same manner as in Example 1 to obtain 2-allyl-3-methyl-4-(2'-hydroxyethylthio)-2-cyclopentenone (20.4 g). Yield, 96 %. nD20 1.5243.

Workup

  1. additionwere charged
  2. customat a temperature of 10° to 20° C
  3. waitat a temperature of 15° to 30° C. for 1 hour
  4. stirringby stirring at the same temperature for 2 hours and at a temperature of 40° to 70° C. for 3 hours
  5. customAfter completion of the reaction
  6. additionthe mixture was treated in the same manner as in Example 1

Sources & evidence

ORD record
ord-0811c84e8090406c8a639b311ef09d9d
Source dataset
uspto-grants-1987_05
Patent number
US04665174

Reaction notes

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