1-Chloromethylnaphthalene → 2-(2-Naphthalen-1-yl-ethyl)-benzonitrile

HRID 2223324Notes

Reaction equation

CN(P([N:9]([CH3:11])C)(N(C)C)=O)C.[Li+].[CH3:13][CH:14]([N-]C(C)C)[CH3:15].Cl[CH2:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1.[CH2:32]1[CH2:36]O[CH2:34][CH2:33]1>>[C:22]1([CH2:21][CH2:34][C:33]2[CH:15]=[CH:14][CH:13]=[CH:36][C:32]=2[C:11]#[N:9])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1

Participants

Reactant 4

HCID 68451-Chloromethylnaphthalene

HCID 8028Tetrahydrofuran

HCID 12679Hexamethylphosphoramide

HCID 2724682Lithium diisopropylamide

Product 1

HCID 227448152-(2-Naphthalen-1-yl-ethyl)-benzonitrileYield 47%

Procedure

A solution of the nitrile (2 mL, 1.0 equiv) and HMPA (3.3 mL, 1.1 equiv) in THF (50 mL) was cooled to −78° C. under an atmosphere of argon. To this solution was added LDA (2 M in THF, 9.4 mL, 1.1 equiv). The dark red solution was allowed to stir for 15 min and then 1-chloromethylnaphthalene (3.3 g, 1.1 equiv) was added. The reaction was quenched after 1.5 hr by the addition of saturated aqueous NH4Cl. The mixture was diluted with EtOAc and water, the organic and aqueous phases separated, and the organic phase further washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography (SiO2, 10% EtOAc in hexane) to give the desired product (2.06 g, 47%).

Workup

customThe reaction was quenched after 1.5 hr by the addition of saturated aqueous NH4Cl
additionThe mixture was diluted with EtOAc and water
customthe organic and aqueous phases separated
washthe organic phase further washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography (SiO2, 10% EtOAc in hexane)

Sources & evidence

ORD record: ord-26280becb86a408db73d3cf4c43ce026
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375125B2

Reaction notes

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