Water → HCID 135725051, compound

HRID 1586330Notes

Reaction equation

HRID 1586330 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-c91362bcec3e45c6aaa5cd3017f8f019
Source dataset
uspto-grants-1999_08
Patent number
US05942530

Reaction notes

Loading…