Tetrahydrofuran → HCID 23130581, compound

HRID 2080168Notes

Reaction equation

HRID 2080168 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[CH2:12]([O:15][CH2:16][CH2:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1)[CH2:13][CH3:14].[OH-].[Na+]>O>[CH2:12]([O:15][CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:22][NH2:23])=[CH:24][CH:25]=1)[CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23130469HCID 23130469, compound

Product 1

HCID 23130581HCID 23130581, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of lithium aluminum hydride (120 mg, 2.5 mmol) and tetrahydrofuran (3 mL) was added 4-(2-propoxy-ethyl)-benzonitrile described in Preparation Example 196 (120 mg, 0.62 mmol), the solution was stirred overnight at room temperature. The reaction solution was cooled to 0° C., tetrahydrofuran (30 mL), water (0.12 mL), an aqueous solution of 5N sodium hydroxide (0.12 mL) and water (0.36 mL) were sequentially added dropwise. After stirring for 1 hour at room temperature, this reaction mixture was filtered through a filter paper. This filtrate was concentrated in vacuao, the residue was filtered using NH-silica gel, and the title compound (123 mg, 0.64 mmol, 103%) was obtained as a colorless oil.

Workup

  1. temperatureThe reaction solution was cooled to 0° C.
  2. stirringAfter stirring for 1 hour at room temperature
  3. filtrationthis reaction mixture was filtered through a filter paper
  4. concentrationThis filtrate was concentrated in vacuao
  5. filtrationthe residue was filtered

Sources & evidence

ORD record
ord-be2472ffec3048e5a373ca36d2ebcfce
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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