Sodium Azide → Azidomethyl 2,2-dimethylpropanoate

HRID 2060722Notes

Reaction equation

HRID 2060722 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([O:11][CH2:12]Cl)(=[O:10])[C:6]([CH3:9])([CH3:8])[CH3:7]>O.CCOC(C)=O>[C:5]([O:11][CH2:12][N:1]=[N+:2]=[N-:3])(=[O:10])[C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 87885Chloromethyl pivalate

Product 1

HCID 11521126Azidomethyl 2,2-dimethylpropanoateYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Sodium azide (1.942 g, 29.9 mmol) was added to a suspension of chloromethyl pivalate (3.00 g, 19.92 mmol) in water (5 mL) and stirred vigorously at 90° C. for 16 h. The reaction mixture was diluted with water (20 mL) and EtOAc (20 ml). The organic layer was washed with brine, dried (Na2SO4) and concentrated to afford azidomethyl pivalate as a liquid (2 g, 64% yield). 1H NMR (400 MHz, Acetone-d6): δ 5.23 (s, 2H), 1.22 (s, 9H).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6fa4f09da12048eeae081608ab749997
Source dataset
uspto-grants-2012_10
Patent number
US08278331B2

Reaction notes

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