Water → HCID 19045637, compound

HRID 1781501Notes

Reaction equation

HRID 1781501 reaction equation
[C:1]([CH2:3][C:4]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:5][CH2:6][C:7](OCC)=[O:8])#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[C:1]([CH2:3][C:4]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:5][CH2:6][CH2:7][OH:8])#[N:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19045624HCID 19045624, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19045637HCID 19045637, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 5-cyano-4,4-diphenylpentanoate (2 g) in tetrahydrofuran (25 ml) was added lithium aluminum hydride (0.37 g) in small portions under ice-cooling. After completion of addition, the mixture was further stirred for 30 minutes. While the reaction mixture was stirred under ice-cooling, water (0.9 ml), 15% aqueous sodium hydroxide (2.7 ml), and water (0.9 ml) were added in the order mentioned. The insoluble matter that separated out was filtered off and the filtrate was extracted with ethyl acetate and saturated aqueous sodium hydrogen carbonate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated to dryness. The group was purified by silica gel column chromatography to provide the title compound (1.3 g) as colorless syrup.

Workup

  1. temperaturecooling
  2. additionAfter completion of addition
  3. stirringWhile the reaction mixture was stirred under ice-
  4. temperaturecooling
  5. customThe insoluble matter that separated out
  6. filtrationwas filtered off
  7. extractionthe filtrate was extracted with ethyl acetate and saturated aqueous sodium hydrogen carbonate
  8. washThe organic layer was washed with saturated aqueous sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated to dryness
  11. customThe group was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d9dc45b335d749a78c3c25428ee98f44
Source dataset
uspto-grants-1997_05
Patent number
US05633248

Reaction notes

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