(+-)-2,6-Dimethyl-5-heptenal → HCID 86702768, compound

HRID 718521Notes

Reaction equation

HRID 718521 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][CH:35]([CH2:38][CH2:39][CH:40]=[C:41]([CH3:43])[CH3:42])[CH:36]=O>>[CH3:42][CH:41]([CH2:40][CH2:39][CH:38]=[C:35]([CH3:36])[CH3:34])[CH:43]=[CH:2][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 61016(+-)-2,6-Dimethyl-5-heptenalHCID 10863251Phenethyltriphenylphosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 86702768HCID 86702768, compoundYield 74.1%

Procedure

Starting from phenethyltriphenylphosphonium bromide (3.20 g, 7.15 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 4.5 mL, 7.15 mmol, 1.0 equiv.) and 2,6-dimethylhept-5-enal (1.51 g, 10.7 mmol, 1.5 equiv.), 1.21 g (74%) of the title compound as a colorless oil was obtained after purification by flash chromatography on SiO2 (cyclohexane/EtOAc 997:3).

Sources & evidence

ORD record
ord-d033b640352f42ea9e6619563f061577
Source dataset
uspto-grants-2015_11
Patent number
US09193935B2

Reaction notes

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