Water → 7-(Benzyloxy)naphthalene-2-carbonitrile

HRID 890954Notes

Reaction equation

HRID 890954 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([C:14]#[N:15])=[CH:11]2)=[CH:6][CH:5]=1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CS(C)=O>[CH2:16]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([C:14]#[N:15])=[CH:11]2)=[CH:6][CH:5]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 222436217-Hydroxynaphthalene-2-carbonitrile

Product 1

HCID 222434287-(Benzyloxy)naphthalene-2-carbonitrileYield 90.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium hydride (151 mg, 60% in mineral oil, 3.77 mmol) is added to a stirring solution of 7-hydroxy-2-naphthonitrile (530 mg, 3.14 mmol) in DMSO (10 mL). After the bubbling subsides, benzyl bromide (448 μL, 3.77 mmol) is added and the resulting mixture is allowed to stir for 4 hours. The reaction mixture is poured into water and extracted with ether. The ether layer is dried (Na2SO4), filtered, and concentrated to dryness. The product is purified by column chromatography (step gradient, 25 to 50% CH2Cl2 in hexanes) to give 7-benzyloxy-2-naphthonitrile (735 mg, 90%) as a white solid. HRMS (EI) calculated for C18H13NO: 259.0997, found 259.0993.

Workup

  1. extractionextracted with ether
  2. dry with materialThe ether layer is dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe product is purified by column chromatography (step gradient, 25 to 50% CH2Cl2 in hexanes)

Sources & evidence

ORD record
ord-312464c0cc5c458b901921ecf26e109d
Source dataset
uspto-grants-2006_02
Patent number
US07001900B2

Reaction notes

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