Lawesson's reagent → HCID 22419730, compound

HRID 1720040Notes

Reaction equation

HRID 1720040 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:12])[CH:5]=[C:6]([CH2:9][O:10][CH3:11])O[CH:8]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:22])=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4](=[O:12])[CH:5]=[C:6]([CH2:9][O:10][CH3:11])[S:22][CH:8]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 32520465-Methoxy-2-(methoxymethyl)-4-pyranone

Product 1

HCID 22419730HCID 22419730, compoundYield 190.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Methoxy-2-(methoxymethyl)-4-pyranone (3.24 g, 19 mmol) (K. Heyns and G. vogelsang, Chem. Ber. 1954, 87, 1377) in toluene (60 ml) was heated at 80° C. with Lawessons reagent (4.23 g, 10 mmol) for 2h. After cooling the reaction mixture was chromatographed on silica gel 60 eluting with toluene/ethyl acetate mixtures to give the title compound (3.54 g, 100%); νmax (CH2Cl2) 3050, 2950, 2830, 1625, and 1560 cm-1 ; δH (CDCl3) 3.4 (3H, s), 3.8 (3H, s), 4.2 (2H, s), 7.3 (1H, s), 7.4 (1H, s); M+ 186.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customwas chromatographed on silica gel 60 eluting with toluene/ethyl acetate

Sources & evidence

ORD record
ord-2102651080fc42629102815031f5681a
Source dataset
uspto-grants-1996_04
Patent number
US05504076

Reaction notes

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