Cesium carbonate → HCID 10670907, compound

HRID 129056

Reaction equation

HRID 129056 reaction equation
C(=O)([O-])[O-:2].[Cs+].[Cs+].[C:7]1([C:13]2[C:14](=[O:18])[O:15][CH2:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[CH2:20][N:21]1[C:31](=[O:32])[C:30]2[C:25](=[CH:26][C:27]([O:36][CH3:37])=[CH:28][C:29]=2[CH:33]([CH3:35])[CH3:34])[S:22]1(=[O:24])=[O:23]>CO.CN(C)C=O>[O:18]=[C:14]1[C:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[C:17]([O:2][CH2:20][N:21]2[C:31](=[O:32])[C:30]3[C:25](=[CH:26][C:27]([O:36][CH3:37])=[CH:28][C:29]=3[CH:33]([CH3:35])[CH3:34])[S:22]2(=[O:24])=[O:23])[CH2:16][O:15]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 99951732-(Chloromethyl)-4-isopropyl-6-methoxybenzo[D]isothiazol-3(2H)-one 1,1-dioxideHCID 10986536HCID 10986536, compound

Product 1

HCID 10670907HCID 10670907, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (0.82 g) was added to a solution of 3-phenyl-2(5H)-furanone (0.88 g) in methanol (15 mL) and the mixture was stirred at room temperature for one hour and stripped of methanol. 2-Chloromethyl-4-isopropyl-6-methoxysaccharin (1.52 g) was added to a solution of the residue in dimethylformamide (15 mL) and the mixture was stirred at room temperature for two days. Silica gel (4.4 g) was added, volatiles were removed under vacuum, and the solid was subjected to flash chromatography on silica gel using ethyl acetate-hexane (3:7) as eluant. Recrystallization of the product from ethanol-ether gave 2-(2,5-dihydro-2-oxo-3-phenylfuran-4-yl)oxymethyl-4-isopropyl-6-methoxysaccharin as a colorless solid (0.45 g, 20% yield, m.r. 180°-182° C. ).

Workup

  1. stirringthe mixture was stirred at room temperature for two days
  2. additionSilica gel (4.4 g) was added
  3. customvolatiles were removed under vacuum
  4. customRecrystallization of the product from ethanol-ether

Sources & evidence

ORD record
ord-1d56cfefff0e479598e4c94eaf10493d
Source dataset
uspto-grants-1995_11
Patent number
US05466701

Linked notes

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