Sodium Sulfite → Sodium 3-[4-Benzo[1,3]dioxol-5-yl-2-(4-methoxy-phenyl)-5-oxo-3-(3,4,5-trimethoxy-benzyl)-2,5-dihydro-furan-2-yloxy]-propane-1-sulfonate

HRID 367036Notes

Reaction equation

HRID 367036 reaction equation
O1CCOCC1.[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[C:17](=[O:47])[O:18][C:19]([O:42][CH2:43][CH2:44][CH2:45]Br)([C:34]4[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=4)[C:20]=3[CH2:21][C:22]3[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=3)=[CH:15][C:10]=2[O:9][CH2:8]1.[S:48]([O-:51])([O-:50])=[O:49].[Na+:52].[Na+].[Na]>O>[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[C:17](=[O:47])[O:18][C:19]([C:34]4[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=4)([O:42][CH2:43][CH2:44][CH2:45][S:48]([O-:51])(=[O:50])=[O:49])[C:20]=3[CH2:21][C:22]3[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=3)=[CH:15][C:10]=2[O:9][CH2:8]1.[Na+:52]

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 312751,4-DioxaneHCID 5360545SodiumHCID 158955113-Benzo[1,3]dioxol-5-yl-5-(3-bromo-propoxy)-5-(4-methoxy-phenyl)-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one

Product 1

HCID 23665776Sodium 3-[4-Benzo[1,3]dioxol-5-yl-2-(4-methoxy-phenyl)-5-oxo-3-(3,4,5-trimethoxy-benzyl)-2,5-dihydro-furan-2-yloxy]-propane-1-sulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 50 mL 1,4-dioxane was added 3-Benzo[1,3]dioxol-5-yl-5-(3-bromo-propoxy)-5-(4-methoxy-phenyl)-4-(3,4,5-trimethoxy-benzyl)5H-furan-2-one 2.0 g (3.19 mmol). A solution of sodium sulfite, 0.88 g (7.0 mmol) in 50 mL water was added, and the mixture was refluxed for 18 hours. The mixture was evaporated in vacuo and the residue was suspended in ethyl ether and water. The suspension was acidified to pH 1 with 2 N HCl, giving an oily precipitate in the aqueous phase. The ether was decanted, and the oil was extracted into ethyl acetate and washed with saturated sodium chloride solution. The organic phase was dried over anhydrous magnesium sulfate, filtered, and diluted with ethyl ether, giving a solid. The solid was filtered and dried in vacuo, giving a white solid, 1.07 g. The product was identified by 1H NMR, MS [M--H]+ =627.3 Da. Elemental analysis indicated the material to contain 1/2 sodium salt per molecule.

Workup

  1. temperaturethe mixture was refluxed for 18 hours
  2. customThe mixture was evaporated in vacuo
  3. customgiving an oily precipitate in the aqueous phase
  4. customThe ether was decanted
  5. extractionthe oil was extracted into ethyl acetate
  6. washwashed with saturated sodium chloride solution
  7. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. additiondiluted with ethyl ether
  10. customgiving a solid
  11. filtrationThe solid was filtered
  12. customdried in vacuo
  13. customgiving a white solid, 1.07 g

Sources & evidence

ORD record
ord-424d7c6b414c470da7b17a992e56d0ef
Source dataset
uspto-grants-2000_10
Patent number
US06133263

Reaction notes

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