Water → HCID 53990727, compound

HRID 2396704Notes

Reaction equation

HRID 2396704 reaction equation
[CH3:1][N:2]([CH3:12])[C:3](=[O:11])[CH2:4]P(=O)(OC)OC.[H-].[Na+].[Br:15][C:16]1[CH:17]=[CH:18][C:19]2[O:23][CH2:22][C:21](=O)[C:20]=2[CH:25]=1.O>C1COCC1>[Br:15][C:16]1[CH:17]=[CH:18][C:19]2[O:23][C:22]([CH2:4][C:3]([N:2]([CH3:1])[CH3:12])=[O:11])=[CH:21][C:20]=2[CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 105127485-Bromobenzo[b]furan-3(2H)-oneHCID 12921478Dimethyl [2-(dimethylamino)-2-oxoethyl]phosphonate

Product 1

HCID 53990727HCID 53990727, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dimethyl [2-(dimethylamino)-2-oxoethyl]phosphonate (5 g) was added to a stirred suspension of sodium hydride (1.02 g of a 60% dispersion in oil) in dry THF (100 ml) at 0° under nitrogen. After stirring for 15 minutes 5-bromo-3-(2H)-benzofuranone (5.0 g) in THF (20 ml) was added dropwise and stirred at room temperature for 3 h. Water (50 ml) was added and the mixture extracted with ethyl acetate (3×50 ml), dried and the solvent removed in vacuo. The crude material was purified by flash chromatography using 50% ethyl acetate/hexane as eluant to yield the title compound as a pale yellow solid m.p. 92°-94° C.

Workup

  1. additionwas added dropwise
  2. extractionthe mixture extracted with ethyl acetate (3×50 ml)
  3. customdried
  4. customthe solvent removed in vacuo
  5. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-4363076e54bd40aba011dea182baa5aa
Source dataset
uspto-grants-1996_02
Patent number
US05494910

Reaction notes

Loading…