Dimethyl Sulfoxide → 4-(3-Cyanopropyl)-6-methoxy-1,2-dihydronaphthalene

HRID 1978007Notes

Reaction equation

HRID 1978007 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[CH2:8][CH2:7][CH:6]=1.[C-:17]#[N:18].[Na+].CS(C)=O>O>[C:17]([CH2:2][CH2:3][CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[CH2:8][CH2:7][CH:6]=1)#[N:18]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 104238234-(3-Bromopropyl)-6-methoxy-1,2-dihydronaphthalene

Product 1

HCID 219964624-(3-Cyanopropyl)-6-methoxy-1,2-dihydronaphthaleneYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(3-bromopropyl)-6-methoxy-1,2-dihydronaphthalene (10 g, 35.6 mmol), sodium cyanide (1.92 g, 39.1 mmol) and dimethyl sulfoxide (20 ml) was stirred for 1 hour at room temperature. The mixture was diluted with water and the product was extracted with ethyl acetate. The extract was washed with brine and water, dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9) to afford the titled compound (7.5 g, yield 93%, oil).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe extract was washed with brine and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9)

Sources & evidence

ORD record
ord-16b9846ffbad43b1a7b9e5c4f050cb33
Source dataset
uspto-grants-2001_05
Patent number
US06235789B1

Reaction notes

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