Water → HCID 16794380, compound

HRID 1901675Notes

Reaction equation

HRID 1901675 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]([CH:19]=[CH:20][CH:21]=1)[O:11][CH2:12][CH:13]([OH:18])[CH2:14][N:15]=[N+]=[N-].O>O1CCCC1>[Cl:7][C:8]1[CH:9]=[C:10]([CH:19]=[CH:20][CH:21]=1)[O:11][CH2:12][CH:13]([OH:18])[CH2:14][NH2:15]

Participants

5

Reactant 3

HCID 962WaterHCID 12031497HCID 12031497, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 16794380HCID 16794380, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.19 g of lithium aluminum hydride was gradually added, whilst ice-cooling and under a stream of nitrogen gas, to a solution of 0.39 g of 3-(3-chlorophenoxy)-2-hydroxypropylazide (prepared as described in Preparation 12) in 5 ml of anhydrous tetrahydrofuran. The mixture was then stirred for a further 1.5 hours under the same conditions, after which excess lithium aluminum hydride was decomposed by adding water. Insolubles were then removed by filtration from the reaction mixture, using a Celite (trade name) filter aid, and the filtrate was dried over anhydrous sodium sulfate. The solvent was then removed from the reaction mixture by evaporation under reduced pressure, to give 0.15 g of the title compound as white crystals, melting at 55° C. to 58° C.

Workup

  1. customInsolubles were then removed by filtration from the reaction mixture
  2. filtrationfilter aid
  3. dry with materialthe filtrate was dried over anhydrous sodium sulfate
  4. customThe solvent was then removed from the reaction mixture by evaporation under reduced pressure

Sources & evidence

ORD record
ord-ba5d5180b05148099b16f51aaa1013c3
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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