Benzyl Bromide → HCID 86672616, compound

HRID 470714Notes

Reaction equation

HRID 470714 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1([O:16][CH3:17])[CH2:15][C:7]2([CH2:10][C:9]([CH2:13][OH:14])([CH2:11][OH:12])[CH2:8]2)[CH2:6]1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+]>O1CCCC1.CN(C)C=O>[CH2:18]([O:14][CH2:13][C:9]1([CH2:11][O:12][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:8][C:7]2([CH2:6][C:5]([O:4][CH3:3])([O:16][CH3:17])[CH2:15]2)[CH2:10]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 68309438HCID 68309438, compound

Product 1

HCID 86672616HCID 86672616, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (755 mg, 17.3 mmol) was added to a dimethylformamide (40 ml)/tetrahydrofuran (20 ml) solution of the compound (1.56 g, 7.20 mmol) obtained in Step 1 above under ice cooling, the resulting mixture was stirred at room temperature for 10 minutes, then benzyl bromide (2.06 ml, 17.3 mmol) was added and the resulting mixture was stirred for 24 hours. Saturated ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography [n-hexane:ethyl acetate=4:1 (v/v)] to give 2.25 g (79%) of the title compound as an oil.

Workup

  1. stirringthe resulting mixture was stirred for 24 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography [n-hexane:ethyl acetate=4:1 (v/v)]

Sources & evidence

ORD record
ord-b46e6a1895c04ccfb7c4ffd4f1291c19
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

Loading…