Sodium Hydroxide → HCID 14352645, compound

HRID 2249329Notes

Reaction equation

HRID 2249329 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C@@H:10]1[C@H:15]([N:16]=[N+]=[N-])[CH2:14][C@H:13]2[CH2:19][C@@H:11]1[C:12]2([CH3:21])[CH3:20].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>CCOCC>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C@@H:10]1[C@H:15]([NH2:16])[CH2:14][C@H:13]2[CH2:19][C@@H:11]1[C:12]2([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14352641HCID 14352641, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14352645HCID 14352645, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 8.64 g of the above-mentioned azide compound 15 in 300 ml of ether is portionwise added 1.2 g of lithium aluminium hydride and the mixture is refluxed under heating for 1 hour. To the reaction mixture is added 10 g of ice and then added 300 ml of 10% aqueous solution of sodium hydroxide. The resulting mixture is shaken well and then the ether layer is collected. The aqueous layer is extracted with ether again. The combined ether layers are washed with water, dried over sodium sulfate, and evaporated under reduced pressure to give 7.56 g of the titled compound 16, of which the physical constant is as follows.

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureunder heating for 1 hour
  3. customthe ether layer is collected
  4. extractionThe aqueous layer is extracted with ether again
  5. washThe combined ether layers are washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-977fb530f0d546bba96ac72448c0265f
Source dataset
uspto-grants-1991_08
Patent number
US05043456

Reaction notes

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