Sodium hydride → 2-(3-Methoxy-phenyl)-8-phenyl-octan-nitrile

HRID 277901Notes

Reaction equation

HRID 277901 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH2:32][C:33]#[N:34])[CH:29]=[CH:30][CH:31]=1.[H-].[Na+]>CN(C=O)C>[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:32]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:33]#[N:34])[CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 88310(3-Methoxyphenyl)acetonitrileHCID 106880386-Phenylhexyl tosylate

Product 1

HCID 226268422-(3-Methoxy-phenyl)-8-phenyl-octan-nitrileYield 54.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By working in a way similar to that described in example 2 but using toluen-4-sulphonic acid 6-phenyl-hexyl ester (5.4 g, 16.24 mmoles), obtained as described in example 11, 3-methoxy-phenyl-acetonitrile (2.39 g, 16.24 mmoles), NaH (55-65%, 715 mg, 17.86 mmoles) and DMF (25 ml), 2.7 g of the title compound were obtained (yield: 54.1%).

Workup

  1. customobtained

Sources & evidence

ORD record
ord-dc215c38cfb646fe9e1b32025bde5c34
Source dataset
uspto-grants-2002_03
Patent number
US06358973B1

Reaction notes

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