Potassium hydroxy sulfite → HCID 178525497, compound

HRID 1868962Notes

Reaction equation

HRID 1868962 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-bd43f320a05a4658853c79d7dbb43f40
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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