Potassium hydroxy sulfite → HCID 178525497, compound

HRID 2078370Notes

Reaction equation

HRID 2078370 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:23])[CH2:19][CH2:20][CH:21]=[O:22])[C:5]2=[O:24].[OH:25]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:23])[CH2:19][CH2:20][C:21]([OH:25])=[O:22])[C:5]2=[O:24]

Participants

4

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 178520681HCID 178520681, compound

Product 1

HCID 178525497HCID 178525497, compoundYield 91.4%

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)-4-oxobutanal (0.2 g, 0.6 mmol) in 3 mL DMF was stirred at room temperature and treated with oxone (0.3 mL, 0.6 mmol). The mixture was stirred at room temperature for 2 hours. The mixture was quenched with 10 mL H2O and adjusted to pH=5 with concentrated HCl. The solid was collected by filtration and washed with 10 mL H2O. The crude product was dissolved in 50 mL EtOAc and washed with 20 mL H2O and then with 20 mL brine. The organic layer was dried over anhydrous Na2SO4, and concentrated in vacuo to give 0.20 g white solid. MS m/e: 365 (M+H)+. Calculated for C18H17ClO6: 364.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. customThe mixture was quenched with 10 mL H2O
  3. filtrationThe solid was collected by filtration
  4. washwashed with 10 mL H2O
  5. dissolutionThe crude product was dissolved in 50 mL EtOAc
  6. washwashed with 20 mL H2O
  7. dry with materialThe organic layer was dried over anhydrous Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-003eb6a386834b60b8854a183dc517ba
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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