Methanol → Ethyl 7-(methylsulfonyl)chromane-2-carboxylate

HRID 39031Notes

Reaction equation

HRID 39031 reaction equation
[CH3:1][S:2]([C:5]1[CH:14]=[C:13]2[C:8]([C:9](=O)[CH:10]=[C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].CO.OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>[Pd].CC(O)=O>[CH3:1][S:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][CH:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 887MethanolHCID 441036D-PsicoseHCID 66878357ethyl 7-(methylsulfonyl)-4-oxo-4H-chromene-2-carboxylate

Product 1

HCID 66879141Ethyl 7-(methylsulfonyl)chromane-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 7-(methylsulfonyl)-4-oxo-4H-chromene-2-carboxylate (1.3 g, 4.4 mmol), palladium on carbon (10%, 0.44 g), MeOH (45 ml) and AcOH (5 ml) was hydrogenated at 40 Psi for 64 h at 60° C. Filtration through Celite (EtOAc) and evaporation followed by filtration through a plug of Al2O3 (EtOAc/ACN) gave the title compound. Yield: 0.6 g. MS m/z (rel. intensity, 70 eV) 307 (64), 302 (91), 286 (14), 285 (M+1, bp), 211 (18).

Workup

  1. filtrationFiltration
  2. customthrough Celite (EtOAc) and evaporation
  3. filtrationfollowed by filtration through a plug of Al2O3 (EtOAc/ACN)

Sources & evidence

ORD record
ord-426a786308d742a7a4d449869c3acf3e
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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