Sodium hydride → HCID 12491978, compound

HRID 993058Notes

Reaction equation

HRID 993058 reaction equation
[C:1]1([CH:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Br:20]N1C(=O)CCC1=O>O1CCCC1.C(Cl)(Cl)Cl>[Br:20][C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 66514Diethyl phenylmalonateHCID 67184N-bromobutanimide

Product 1

HCID 12491978HCID 12491978, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of diethyl 2-phenylmalonate (15 ml) in 200 ml of tetrahydrofuran, kept at 0° C. and under nitrogen atmosphere, 3.475 g of sodium hydride are added and the mixture is kept 30 minutes under stirring at 0° C., then it is brought to room temperature. After cooling again to 0° C., the reaction mixture is added with 14.3 g of N-bromosuccinimide. After about 15 minutes, the white solid which separated is filtered off and the filtrate is concentrated to dryness to give a residue which is redissolved in chloroform and dried over sodium sulfate. The solvent is evaporated under reduced pressure to give 15.66 g of the product.

Workup

  1. customkept at 0° C. and under nitrogen atmosphere
  2. customis brought to room temperature
  3. temperatureAfter cooling again to 0° C.
  4. waitAfter about 15 minutes
  5. customthe white solid which separated
  6. filtrationis filtered off
  7. concentrationthe filtrate is concentrated to dryness
  8. customto give a residue which
  9. dry with materialdried over sodium sulfate
  10. customThe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-8a65b66a83d44126a457808315e974bb
Source dataset
uspto-grants-2002_10
Patent number
US06472396B1

Reaction notes

Loading…