trans-2,cis-6-Nonadienal → (4E,8Z)-Undeca-2.4.8-trienylbenzene

HRID 718518Notes

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](=O)/[CH:35]=[CH:36]/[CH2:37][CH2:38]/[CH:39]=[CH:40]\[CH2:41][CH3:42]>>[CH2:3]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH:2]=[CH:34]/[CH:35]=[CH:36]/[CH2:37][CH2:38]/[CH:39]=[CH:40]\[CH2:41][CH3:42]

Participants

Reactant 3

HCID 643731trans-2,cis-6-Nonadienal

HCID 10863251Phenethyltriphenylphosphonium bromide

HCID 178418339Butyllithium

Product 1

HCID 86702765(4E,8Z)-Undeca-2.4.8-trienylbenzeneYield 61%

Procedure

Starting from phenethyltriphenylphosphonium bromide (3.05 g, 6.82 mmol, 1.0 equiv.), n-BuLi (1.6M in hexanes, 4.3 mL, 6.82 mmol, 1.0 equiv.) and (2E,6Z)-nona-2,6-dienal (1.41 g, 10.2 mmol, 1.5 equiv.), 0.94 g (61%) 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-8b96fa257a3d43b19945964fea6d4d71
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193935B2

Reaction notes

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