Water → HCID 23130535, compound

HRID 2080136Notes

Reaction equation

HRID 2080136 reaction equation
[CH3:1][C:2]([CH3:11])=[CH:3][C:4]1[S:8][C:7]([C:9]#[N:10])=[CH:6][CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][C:2]([CH3:11])=[CH:3][C:4]1[S:8][C:7]([CH2:9][NH2:10])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23130374HCID 23130374, compound

Product 1

HCID 23130535HCID 23130535, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(2-Methylpropenyl)-thiophene-2-carbonitrile described in Preparation Example 144 (15 mg, 0.092 mmol) was dissolved in tetrahydrofuran (2 mL), lithium aluminum hydride (10 mg, 0.26 mmol) was added under stirring at room temperature, the solution was heated to 70° C., followed by stirring for 2 hours. The reaction solution was cooled on an ice bath, then, water (0.01 mL), an aqueous solution of 15% sodium hydroxide (0.01 mL) and water (0.03 mL) were sequentially added, then, the solid was filtered, and washed with tetrahydrofuran (5 mL). The filtrate and the washings were combined, and dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo, and the title compound (14 mg, 0.083 mmol, 91.1%) was obtained as a colorless oil.

Workup

  1. temperaturethe solution was heated to 70° C.
  2. stirringby stirring for 2 hours
  3. temperatureThe reaction solution was cooled on an ice bath
  4. filtrationthe solid was filtered
  5. washwashed with tetrahydrofuran (5 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-dc0f40ed58884193ae6e32006ce0eaac
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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