Water → HCID 67146787, compound

HRID 2422224Notes

Reaction equation

HRID 2422224 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]#[N:21])=[CH:14][CH:13]=1)[CH2:6][CH2:5]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[C:29](OC(=O)C)(=[O:31])[CH3:30]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][CH2:20][NH:21][C:29](=[O:31])[CH3:30])=[CH:16][CH:17]=1)[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 962Water2×HCID 7918Acetic AnhydrideHCID 21226445Aluminium lithium hydrideHCID 67146897HCID 67146897, compound

Product 1

HCID 67146787HCID 67146787, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[(5-chloro-2,3-dihydro-1H-inden-1-yl)oxy]benzenepropanenitrile (0.50 g, 1.7 mmol) in tetrahydrofuran (25 mL) was added lithium aluminum hydride (77 mg, 2.0 mmol) under ice-cooling, and the mixture was stirred in an ice bath for 3 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The obtained oil was dissolved in pyridine (20 mL), acetic anhydride (0.18 mL, 0.95 mmol) was added, and the mixture was stirred at room temperature for 3 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (0.11 g, yield 18%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe obtained oil was dissolved in pyridine (20 mL)
  6. stirringthe mixture was stirred at room temperature for 3 hrs
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe extract was washed with water
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-75fd47dff66e43548bf658ba89174e77
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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