Water → 1426531-82-9

HRID 335332Notes

Reaction equation

HRID 335332 reaction equation
[N:1]([CH2:4][CH:5]1[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][CH2:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[CH3:10][C:8]1([CH3:11])[O:9][CH:5]([CH2:4][NH2:1])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86695687HCID 86695687, compound

Product 1

HCID 754816151426531-82-9

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

5-(Azidomethyl)-2,2-dimethyltetrahydrofuran (22 g, 142 mmol) in THF (500 ml) was treated with Triphenylphosphine (39.0 g, 149 mmol) and t stirred for 5 mins. Water (50.0 ml) was added and the reaction mixture was heated at 80° C. for 4 hrs. The mixture was passed through Isolute® SCX-2 resin (200 g 0.67 mmol/g) eluting with MeOH (500 ml), DMSO (100 ml), 20% MeOH:DCM (500 ml), MeOH (500 ml) followed 7M ammonia in MeOH (500 ml). The ammonia layer was evaporated to dryness to afford the title compound.

Workup

  1. washeluting with MeOH (500 ml), DMSO (100 ml), 20% MeOH
  2. customThe ammonia layer was evaporated to dryness

Sources & evidence

ORD record
ord-2cf5a4f17b3a457a928f2591c5ae192c
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

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