Thiophenol → HCID 13176138, compound

HRID 978621Notes

Reaction equation

HRID 978621 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH2:15]([CH:20]1[CH:24]([OH:25])[CH:23]=[CH:22][C:21]1=O)[CH2:16][CH2:17][CH2:18][CH3:19]>COC1C=CC2N=CC=C([C@@H](O)[C@H]3N4C[C@H](C=C)[C@@H](CC4)C3)C=2C=1.C1(C)C=CC=CC=1>[CH2:15]([C:20]1[C:24](=[O:25])[CH2:23][CH:22]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:21]=1)[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 131761314-Hydroxy-5-pentylcyclopent-2-en-1-one

Product 1

HCID 13176138HCID 13176138, compoundYield 104.5%

Reagents, catalysts & solvents 2

HCID 3034034QuinineCatalystHCID 1140TolueneSolvent

Procedure

Into the same flask as used in Example 1, thiophenol (10 g), triethylamine (2 g), quinine (0.2 g), 2-n-pentyl-3-hydroxy-4-cyclopentenone (16.8 g) and toluene (30 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 treated and purified in the same manner as in Example 50 to obtain 2-n-pentyl-4-phenylthio-2-cyclopentenone (24.7 g). Yield, 95%. nD20 1.5706.

Workup

  1. additionwere charged
  2. customAfter completion of the reaction
  3. additionthe mixture was treated
  4. custompurified in the same manner as in Example 50

Sources & evidence

ORD record
ord-4132d1e1e12149ad9de706bb0f9bd7c5
Source dataset
uspto-grants-1987_05
Patent number
US04665174

Reaction notes

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