Water → HCID 135725051, compound

HRID 1279921Notes

Reaction equation

HRID 1279921 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[S:17][CH:18]=[C:19]([CH2:21][C:22](OCC)=[O:23])[N:20]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[C:12]([C:9]1[CH:8]=[C:7]([C:16]2[S:17][CH:18]=[C:19]([CH2:21][CH2:22][OH:23])[N:20]=2)[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:10]=1[OH:11])([CH3:13])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 962Water3×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 135725081HCID 135725081, compound

Product 1

HCID 135725051HCID 135725051, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of Step D 5.0 g (13.33 mmole), was dissolved in 95 ml tetrahydrofuran with stirring, under nitrogen. Solid lithium aluminum hydride, 760 mg (20 mmole), was cautiously added. There was much bubbling. The mixture was stirred under nitrogen for 1 hour. Water, 0.76 ml H2O, was cautiously added followed by 0.76 ml 15% sodium hydroxide, followed by 2.3 ml water. The inorganics were filtered off and the filtrate was stripped, dissolved in ethyl acetate, washed once with 1 N hydrochloric acid, twice with brine, and stripped to give 4.42 g (99%) product which was used without further purification.

Workup

  1. stirringThe mixture was stirred under nitrogen for 1 hour
  2. filtrationThe inorganics were filtered off
  3. dissolutiondissolved in ethyl acetate
  4. washwashed once with 1 N hydrochloric acid, twice with brine

Sources & evidence

ORD record
ord-6a8f4c75159444b59bccee71381511d4
Source dataset
uspto-grants-2002_09
Patent number
US06448396B2

Reaction notes

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