2-Acetylnaphthalene → HCID 86702767, compound

HRID 718520Notes

Reaction equation

HRID 718520 reaction equation
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Li]CCCC.[CH:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][C:35]=1[C:44](=O)[CH3:45]>>[C:38]1([CH2:37][CH:36]=[C:35]([C:44]2[CH:2]=[CH:3][C:4]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:45]=2)[CH3:34])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

4

Reactant 3

HCID 71222-AcetylnaphthaleneHCID 10863251Phenethyltriphenylphosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 86702767HCID 86702767, compoundYield 54%

Procedure

Starting from phenethyltriphenylphosphonium bromide (2.30 g, 5.14 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 3.2 mL, 5.14 mmol, 1.0 equiv.) and 1-(naphthalen-2-yl)ethanone (1.22 g, 7.20 mmol, 1.4 equiv.), 0.71 g (54%) of the title compound as a yellow oil was obtained after purification by flash chromatography on SiO2 (cyclohexane/EtOAc 995:5).

Sources & evidence

ORD record
ord-5d99183ba7564bc79b21aaa3b7172510
Source dataset
uspto-grants-2015_11
Patent number
US09193935B2

Reaction notes

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