Potassium → HCID 76420551, compound

HRID 540655Notes

Reaction equation

HRID 540655 reaction equation
[OH:1][CH:2]([C:8]1[O:12][C:11]2[C:13]([O:23]C)=[C:14]3[C:19](=[C:20]([O:21]C)[C:10]=2[CH:9]=1)[CH:18]=[CH:17][CH:16]=[CH:15]3)[CH2:3][S:4]([CH3:7])(=[O:6])=[O:5].[N+]([O-])([O-])=O.[NH4+].[Ce].[K]>C(#N)C.O>[OH:1][C:2]([C:8]1[O:12][C:11]2[C:13](=[O:23])[C:14]3[C:19]([C:20](=[O:21])[C:10]=2[CH:9]=1)=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:3][S:4]([CH3:7])(=[O:6])=[O:5]

Participants

5

Reactant 3

HCID 5462222PotassiumHCID 57418452Ammonium cerium-nitrateHCID 86686937HCID 86686937, compound

Product 1

HCID 76420551HCID 76420551, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent2×

Procedure

To a solution of crude 2-(1-hydroxyl-2-methylsulfonylethyl)-4,9-dimethoxy-naphtho[2,3-b]furan from previous step in 40 mL of acetonitrile/water (4:1) in an ice bath, a solution of 4.4 grams (8 mmoles) of cerium ammonium nitrate and 1.34 gram (8 mmoles) of potassium bromated in 40 mL of acetonitrile/water (1:4) was added dropwise over 20 minutes. The resulting mixture was further stirred for 120 minutes in an ice bath, and then was evaporated to remove acetonitrile. The remaining aqueous solution was extracted with dichloromethane twice. The combined organic phase was washed with water, dried with anhydrous sodium sulfate, and evaporated to dryness. The residue was subjected to silica gel chromatograph purification using dichloromethane/ethyl acetate (4:1) as elution solvent. 0.64 gram (2 mmoles) of product was obtained with overall yield of 51% and characterized by 1H NMR and mass spectrum. 1H NMR (in CDCl3) δ 3.20 (s, 3H), 4.68 (s, 2H), 7.84-7.87 (m, 3H), 8.23-8.33 (m, 2H). Mass (M+H) is 319.

Workup

  1. additionwas added dropwise over 20 minutes
  2. customwas evaporated
  3. customto remove acetonitrile
  4. extractionThe remaining aqueous solution was extracted with dichloromethane twice
  5. washThe combined organic phase was washed with water
  6. dry with materialdried with anhydrous sodium sulfate
  7. customevaporated to dryness
  8. customThe residue was subjected to silica gel chromatograph purification
  9. washas elution solvent

Sources & evidence

ORD record
ord-37c3189d408940a3823e1cb2f1dcb3cc
Source dataset
uspto-grants-2014_10
Patent number
US08871802B2

Reaction notes

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