Sodium Azide → 4-(azidomethyl)tetrahydro-2H-pyran

HRID 1752547Notes

Reaction equation

HRID 1752547 reaction equation
I[CH2:2][CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[N-:9]=[N+:10]=[N-:11].[Na+]>CS(C)=O.C(OCC)C>[N:9]([CH2:2][CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)=[N+:10]=[N-:11]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 27955074-(Iodomethyl)oxane

Product 1

HCID 594860844-(azidomethyl)tetrahydro-2H-pyran

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

4-(Iodomethyl)tetrahydro-2H-pyran (4.76 g, 21.1 mmol) was dissolved in dimethyl sulfoxide (25 mL). Sodium azide (2.70 g, 41.5 mmol) was added and the mixture was stirred at ambient temperature overnight. The resulting slurry was diluted with diethyl ether and washed with water. The organic layer was concentrated under reduced pressure to afford the title compound. The product was used directly in subsequent reactions without characterization.

Workup

  1. washwashed with water
  2. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3e6b32b49a124c4b9d5ae6593f5eb617
Source dataset
uspto-grants-2015_10
Patent number
US09163007B2

Reaction notes

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