Benzyl Bromide → HCID 15485709, compound

HRID 368377Notes

Reaction equation

HRID 368377 reaction equation
[N:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[OH:10])=[N+:2]=[N-:3].[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[CH2:13]([O:10][C@@H:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C@H:4]1[N:1]=[N+:2]=[N-:3])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10953608HCID 10953608, compound

Product 1

HCID 15485709HCID 15485709, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-azidocyclohexylalcohol (1 g, 7.1 mmol) in THF (10 mL), sodium hydride (284 mg, 7.1 mmol) was added. After 10 minutes, benzyl bromide (0.84 mL, 7.1 mmol) was added. The reaction mixture was partitioned between ethyl acetate and NaHCO3 (aq.). The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure and chromatography of the resulting liquid on silica gel (hexane: ethyl acetate; 10:1) gave product (1.4 g, 85%). EI-MS m/z 232 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and NaHCO3 (aq.)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure and chromatography of the resulting liquid on silica gel (hexane: ethyl acetate; 10:1)

Sources & evidence

ORD record
ord-5f677ab4fa0d408e9ad3124916f260a1
Source dataset
uspto-grants-2000_10
Patent number
US06133319

Reaction notes

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