Sulfamic Acid → 3-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid

HRID 1279418Notes

Reaction equation

HRID 1279418 reaction equation
[CH:1]([C:3]1[O:4][C:5]([CH3:18])=[CH:6][C:7](=[O:17])[C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:2].S(=O)(=O)([OH:21])N.Cl([O-])=O.[Na+]>CC(C)=O.O>[C:1]([C:3]1[O:4][C:5]([CH3:18])=[CH:6][C:7](=[O:17])[C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([OH:21])=[O:2]

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 120111872-Formyl-3-benzyloxy-6-methyl-pyran-4(1H)-oneHCID 23668197Sodium Chlorite

Product 1

HCID 98564973-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

2-Formyl-3-benzyloxy-6-methyl-pyran-4(1H)-one (3.67 g, 15.03 mmol, 1 eq) was dissolved in acetone (50 ml) and the solution diluted with water (50 ml). To the reaction mixture was added sulfamic acid (2.04 g, 21.04 mmol, 1.4 eq) and 80% sodium chlorite (1.78 g, 15.8 mmol, 1.05 eq) and allowed to stir for 1 hour at room temperature in an open vessel. Removal of acetone in vacuo yielded crude product as a precipitate in the remaining aqueous solution. The solid was collected, washed with absolute ethanol and dried (3.32 g, 85%). m.p. 173-175° C.

Workup

  1. customRemoval of acetone in vacuo
  2. customyielded crude product as a precipitate in the remaining aqueous solution
  3. customThe solid was collected
  4. washwashed with absolute ethanol
  5. customdried (3.32 g, 85%)

Sources & evidence

ORD record
ord-afd77f03c690489da09785c508822764
Source dataset
uspto-grants-2002_09
Patent number
US06448273B1

Reaction notes

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