Sulfamic Acid → 5-(4-methoxybenzyloxy)-4-oxo-4H-pyran-2-carboxylic acid

HRID 525851Notes

Reaction equation

HRID 525851 reaction equation
[OH:1][CH2:2][C:3]1[O:4][CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:7](=[O:9])[CH:8]=1.C(N(CC)CC)C.S(=O)(=O)([OH:29])N.Cl([O-])=O.[Na+]>C(Cl)(Cl)Cl.CC(C)=O.O.CS(C)=O>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][O:10][C:6]2[C:7](=[O:9])[CH:8]=[C:3]([C:2]([OH:29])=[O:1])[O:4][CH:5]=2)=[CH:17][CH:16]=1

Participants

9

Reactant 4

HCID 5987Sulfamic AcidHCID 8471TriethylamineHCID 104916984H-Pyran-4-one, 2-(hydroxymethyl)-5-[(4-methoxyphenyl)methoxy]-HCID 23668197Sodium Chlorite

Product 1

HCID 150777735-(4-methoxybenzyloxy)-4-oxo-4H-pyran-2-carboxylic acidYield 54.2%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(hydroxymethyl)-5-((4-methoxybenzyl)oxy)-4H-pyran-4-one (2.57 g, 9.80 mmol) in chloroform (45 ml) was added dimethyl sulfoxide (12 ml) and triethylamine (8.20 ml, 58.8 mmol). The mixture was cooled to 0° C., and sulfur trioxide, pyridine salt (3.96 ml, 49.0 mmol) was added. The mixture was allowed to warm to room temperature and stirred for 20 h. The resulting precipitate was filtered and washed with water. The filtrate was washed with water and the phases were separated. The organic layer was concentrated and combined with the precipitate. Water (20.0 ml), acetone (20.0 ml) and sulfamic acid (1.431 g, 14.74 mmol) were added, followed by sodium chlorite (1.332 g, 14.73 mmol) and the mixture was allowed to stir at room temperature for 70 h. The resulting precipitate was filtered, washed with water and acetone, and dried to give, 5-((4-methoxybenzyl)oxy)-4-oxo-4H-pyran-2-carboxylic acid (1.466 g, 5.31 mmol, 54.2% yield) as white solid. LCMS: (M+Na)+: 299.0.

Workup

  1. temperatureto warm to room temperature
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. washThe filtrate was washed with water
  5. customthe phases were separated
  6. concentrationThe organic layer was concentrated
  7. stirringto stir at room temperature for 70 h
  8. filtrationThe resulting precipitate was filtered
  9. washwashed with water and acetone
  10. customdried
  11. customto give

Sources & evidence

ORD record
ord-da97ac393dda4e85a179c73ab856c7cc
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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