Water → HCID 69300599, compound

HRID 2196531Notes

Reaction equation

HRID 2196531 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[C:14]#[N:15])[N:9]=[C:8]([C:19]([F:22])([F:21])[F:20])[CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:12]=[C:13]([CH2:14][NH2:15])[CH:16]=[CH:17][CH:18]=2)[N:9]=[C:8]([C:19]([F:21])([F:20])[F:22])[CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 15880986284463-59-8HCID 21226445Aluminium lithium hydride

Product 1

HCID 69300599HCID 69300599, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 53 (3 g, 9.89 mmol) in THF (50 mL) at 0° C. was added lithium aluminium hydride (0.939 g, 24.73 mmol). The resulting suspension was allowed to stir for 0.5 h. The reaction mixture was then warmed to room temperature and stirred for another 1 h. The following was added sequentially: 0.9 mL of water, 0.9 mL of 15% NaOH and 1.8 mL of water. The white solid was removed by filtration and the filtrate evaporated under vacuum. The title product 54 (3.04 g, 100% yield) was isolated as a pale yellow oil. Crude was used without any further purification. LRMS (ESI): calc. 307.3; found 308.4 (MH)+.

Workup

  1. stirringstirred for another 1 h
  2. additionThe following was added sequentially
  3. customThe white solid was removed by filtration
  4. customthe filtrate evaporated under vacuum

Sources & evidence

ORD record
ord-7c3ac86c7c5f4d36a3db2df3297dfda9
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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