Water → HCID 20026708, compound

HRID 1723091Notes

Reaction equation

HRID 1723091 reaction equation
[CH3:1][CH:2]1[C:12]2[C:13]3[C:8]([CH:9]=[CH:10][CH:11]=2)=[CH:7][CH:6]=[CH:5][C:4]=3[C:3]1=[O:14].[H-].[Na+].Br[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[N:26])[CH:20]=1.O>O1CCCC1.C(OCC)C>[CH3:1][C:2]1([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[N:26])[CH:20]=2)[C:12]2[C:13]3[C:8]([CH:9]=[CH:10][CH:11]=2)=[CH:7][CH:6]=[CH:5][C:4]=3[C:3]1=[O:14]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 130673162-Methylacenaphthylen-1(2H)-one

Product 1

HCID 20026708HCID 20026708, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 2-methyl-1-acenaphthenone (1.00 g, 0.005 mole) in tetrahydrofuran (20.0 ml) was added dropwise to a solution of sodium hydride (0.580 g, 0.024 mole, 50% oil dispersion) in tetrahydrofuran (35.0 ml) at 0°. The reaction mixture was stirred for 2 hours at room temperature. At 0°, α-Bromo-m-tolunitrile (1.37 g, 0.007 mole) in tetrahydrofuran (10.0 ml) was added dropwise. The mixture was stirred for 24 hours at room temperature, poured into water, and isolated by extraction with diethyl ether. The material was chromatographed on silica with ethylacetate/hexane providing the title compound as an oil (1.55 g, 95%).

Workup

  1. stirringThe mixture was stirred for 24 hours at room temperature
  2. customThe material was chromatographed on silica with ethylacetate/hexane providing the title compound as an oil (1.55 g, 95%)

Sources & evidence

ORD record
ord-9e86ca993d2049e1baf84246ce83afe1
Source dataset
uspto-grants-1989_08
Patent number
US04859697

Reaction notes

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