2-Acetylnaphthalene → 2-(4-(4-Methoxyphenyl)but-2-en-2-yl)naphthalene

HRID 718532Notes

Reaction equation

HRID 718532 reaction equation
[Br-].[CH3:2][O:3][C:4]1[CH:30]=[CH:29][C:7]([CH2:8][CH2:9][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:6][CH:5]=1.[Li]CCCC.[CH:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=[CH:38][C:37]=1[C:46](=O)[CH3:47]>>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH:9]=[C:46]([C:37]2[CH:38]=[CH:39][C:40]3[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH:36]=2)[CH3:47])=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 71222-AcetylnaphthaleneHCID 85891800p-Methoxyphenethyltriphenylphosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 679827372-(4-(4-Methoxyphenyl)but-2-en-2-yl)naphthaleneYield 48.3%

Procedure

Starting from p-methoxyphenethyltriphenylphosphonium bromide (3.15 g, 6.60 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 4.2 mL, 6.60 mmol, 1.0 equiv.) and 1-(naphthalen-2-yl)ethanone (1.69 g, 9.90 mmol, 1.5 equiv.), 0.92 g (48%) of the title compound as a yellow oil was obtained after purification by flash chromatography on SiO2 (hexanes/EtOAc 995:5→99:1).

Sources & evidence

ORD record
ord-52b85ca40836468b8abf4305f43af5e6
Source dataset
uspto-grants-2015_11
Patent number
US09193935B2

Reaction notes

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