Benzyl Bromide → HCID 53819314, compound

HRID 976048Notes

Reaction equation

HRID 976048 reaction equation
[H-].[Na+].[C:3]1([CH2:13][CH:14]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1>[C:3]1([CH2:13][C:14]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 54143623HCID 54143623, compound

Product 1

HCID 53819314HCID 53819314, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 2.96 g (0.062 mol) of NaH. oil (50%) was washed with THF to remove the oil, then suspended in 300 mL THF, and then treated with 20.0 g (0.056 mol) of di-t-butyl (1-naphthylmethyl)malonate. The solution was refluxed for 40 minutes, then cooled to room temperature. A solution of 6.8 mL (0.057 mol) of benzyl bromide in 40 mL THF was then added and the mixture heated at reflux for 15 minutes, then left stirring at room temperature overnight. The solvent was removed under reduced pressure and the residue taken up in EtOAc and washed with 1N citric acid, saturated NaCl, saturated NaHCO3, and saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure left 25 g of a yellow oil. Chromatography on silica gel, eluting with hexane:EtOAc (90:10) gave 20.0 g (80% yield) of the product as a clear oil. The structure was confirmed by NMR and mass spectroscopy.

Workup

  1. washoil (50%) was washed with THF
  2. customto remove the oil
  3. temperatureThe solution was refluxed for 40 minutes
  4. temperaturethe mixture heated
  5. temperatureat reflux for 15 minutes
  6. waitleft
  7. customThe solvent was removed under reduced pressure
  8. washwashed with 1N citric acid, saturated NaCl, saturated NaHCO3, and saturated NaCl
  9. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
  10. waitleft 25 g of a yellow oil
  11. washChromatography on silica gel, eluting with hexane:EtOAc (90:10)

Sources & evidence

ORD record
ord-6f65b0f377884ab083c521a4bc4d9f4a
Source dataset
uspto-grants-1997_03
Patent number
US05610177

Reaction notes

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