Potassium hydroxy sulfite → HCID 178454737, compound

HRID 2078371Notes

Reaction equation

HRID 2078371 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[C:8]1([CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[C:7]([OH:17])=[C:6]([C:18](=[O:24])[CH:19]([CH3:23])[CH2:20][CH:21]=[O:22])[C:5]2=[O:25].[OH:26]OS([O-])=O.[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[C:8]1([CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[C:7]([OH:17])=[C:6]([C:18](=[O:24])[CH:19]([CH3:23])[CH2:20][C:21]([OH:26])=[O:22])[C:5]2=[O:25]

Participants

4

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 178450774HCID 178450774, compound

Product 1

HCID 178454737HCID 178454737, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(6-chloro-2-hydroxy-4-oxo-2′,3′,5′,6′-tetrahydro-4H-spiro[naphthalene-1,4′-pyran]-3-yl)-3-methyl-4-oxobutanal (0.1 g, 0.3 mmol) in 2 mL DMF was stirred at room temperature and treated with oxone (0.2 mL, 0.3 mmol). The mixture was stirred at room temperature for 2 hours. The mixture was quenched with 20 mL H2O, and the pH was adjusted to pH=5 with concentrated HCl. The precipitate that formed was collected by filtration and washed with 20 mL water. The product was dried under high vacuum to give 0.1 g of the product as an off-white solid. MS m/z 379 (M+H)+. Calculated for C19H19ClO6: 378.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. customThe mixture was quenched with 20 mL H2O
  3. customThe precipitate that formed
  4. filtrationwas collected by filtration
  5. washwashed with 20 mL water
  6. customThe product was dried under high vacuum

Sources & evidence

ORD record
ord-f74d76a6e851495ebe1fd279e6e19d3d
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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