Water → Methyl 5-azidopentanoate

HRID 1616612Notes

Reaction equation

HRID 1616612 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11].O>CS(C)=O>[CH3:13][O:12][C:10](=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6][N:1]=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 79557Methyl 5-bromovalerate

Product 1

HCID 14562330Methyl 5-azidopentanoateYield 100.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Add sodium azide (12.5 g, 193 mmol) to a rapidly stirred solution of methyl 5-bromovalerate (25.08 g, 129 mmol) in DMSO (200 mL, anhydrous). Stir at room temperature overnight under N2. Add water (400 mL) and stir for 30 minutes. Extract with Et2O (×3) and wash combined Et2O layers with brine (×3). Dry organic layer over MgSO4 and concentrate to give the title compound (20.3 g, 100%).

Workup

  1. extractionExtract with Et2O (×3)
  2. washwash
  3. concentrationDry organic layer over MgSO4 and concentrate

Sources & evidence

ORD record
ord-6330a2cef44142a79c7474e5397896b3
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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