(3E)-3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one → HCID 86702764, compound

HRID 718517Notes

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.[CH3:34]/[C:35](=[CH:39]\[CH:40]1[C:45]([CH3:47])([CH3:46])[CH2:44][CH2:43][CH:42]=[C:41]1[CH3:48])/[C:36](=O)[CH3:37]>>[CH3:37][C:36](/[C:35](/[CH3:34])=[CH:39]/[CH:40]1[C:45]([CH3:47])([CH3:46])[CH2:44][CH2:43][CH:42]=[C:41]1[CH3:48])=[CH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Reactant 3

HCID 5372174(3E)-3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one

HCID 10863251Phenethyltriphenylphosphonium bromide

HCID 178418339Butyllithium

Product 1

HCID 86702764HCID 86702764, compoundYield 20%

Procedure

Starting from phenethyltriphenylphosphonium bromide (2.80 g, 6.26 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 3.9 mL, 6.26 mmol, 1.0 equiv.) and (E)-3-methyl-4-(2,6,6-trimethylcyclohex-2-enyl)but-3-en-2-one (1.94 g, 9.39 mmol, 1.5 equiv.), 0.36 g (20%) of the title compound as a colorless oil was obtained after purification by flash chromatography on SiO2 (cyclohexane/EtOAc 995:5).

Sources & evidence

ORD record: ord-842d6a6ae11d47fa9dc13df6c2a5732d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193935B2

Reaction notes

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