Water → 4-(3-Oxo-2-phenylheptyl)-benzonitrile

HRID 2260827Notes

Reaction equation

HRID 2260827 reaction equation
[H-].[Na+].[C:3]1([CH2:9][C:10](=[O:15])[CH2:11][CH2:12][CH2:13][CH3:14])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1.O>O1CCCC1>[O:15]=[C:10]([CH2:11][CH2:12][CH2:13][CH3:14])[CH:9]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH2:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 331911-Phenyl-2-hexanoneHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 189990744-(3-Oxo-2-phenylheptyl)-benzonitrileYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

240 mg of sodium hydride as a suspension at 50% in oil were added to a solution of 0.81 g of 1-phenyl-2-hexanone of Step A of Example 7 in 20 ml of tetrahydrofuran and the mixture was stirred for 90 minutes at 40° C. Then, a solution of 900 mg of 4-(bromomethyl)-benzonitrile in 10 ml of tetrahydrofuran was added and after stirring for 2 hours at ambient temperature, the reaction mixture was poured into water. Extraction was carried out with ethyl acetate and the extracts were washed with water, dried, and evaporated to dryness. The residue was chromatographed on silica (eluant: methylene chloride--hexane (1-1)) to obtain 1.1 g of the desired product melting at 70° C.

Workup

  1. stirringafter stirring for 2 hours at ambient temperature
  2. extractionExtraction
  3. washthe extracts were washed with water
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was chromatographed on silica (eluant: methylene chloride--hexane (1-1))

Sources & evidence

ORD record
ord-c01a801199b34d1b8c63c589dac26e8e
Source dataset
uspto-grants-1995_12
Patent number
US05478938

Reaction notes

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