Toluene → HCID 135965991, compound

HRID 1614888Notes

Reaction equation

HRID 1614888 reaction equation
[CH3:1][C:2]([C:4]1[C:13]([OH:14])=[CH:12][C:11]2[C:10]([CH3:16])([CH3:15])[CH2:9][CH2:8][C:7]([CH3:18])([CH3:17])[C:6]=2[CH:5]=1)=O.C1(C)C=CC=CC=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1>O>[OH:14][C:13]1[C:4]([C:2](=[S:35])[CH3:1])=[CH:5][C:6]2[C:7]([CH3:18])([CH3:17])[CH2:8][CH2:9][C:10]([CH3:16])([CH3:15])[C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 87949Lawesson's reagentHCID 2266995,6,7,8-Tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl methyl ketone

Product 1

HCID 135965991HCID 135965991, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To 5,6,7,8-tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl methyl ketone (13.3 mg, 53.9 μmol) were added anhydrous toluene (1 mL) and Lawesson's reagent (32.0 mg, 80.9 mmol) followed by stirring at 120° C. for 24 hours. The reaction solution was poured into cold water and extracted by dichloromethane, and the combined organic layers were concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using hexane/ethyl acetate (12/1) as an elution solvent. The yield was 4.2 mg (30%).

Workup

  1. extractionextracted by dichloromethane
  2. concentrationthe combined organic layers were concentrated under reduced pressure
  3. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-93356178ab5f4aeeb11449bfb9ef3de0
Source dataset
uspto-grants-2014_07
Patent number
US08765719B2

Reaction notes

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