Lilial → HCID 86702774, compound

HRID 718533Notes

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.[C:36]([C:40]1[CH:45]=[CH:44][C:43]([CH2:46][CH:47]([CH3:50])[CH:48]=O)=[CH:42][CH:41]=1)([CH3:39])([CH3:38])[CH3:37]>>[C:36]([C:40]1[CH:41]=[CH:42][C:43]([CH2:46][CH:47]([CH3:50])[CH:48]=[CH:9][CH2:8][C:7]2[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:30][CH:29]=2)=[CH:44][CH:45]=1)([CH3:39])([CH3:38])[CH3:37]

Participants

Reactant 3

HCID 228987Lilial

HCID 85891800p-Methoxyphenethyltriphenylphosphonium bromide

HCID 178418339Butyllithium

Product 1

HCID 86702774HCID 86702774, compoundYield 51.1%

Procedure

Starting from p-methoxyphenethyltriphenylphosphonium bromide (3.10 g, 6.49 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 4.1 mL, 6.49 mmol, 1.0 equiv.) and 3-(4-tert-butylphenyl)-2-methylpropanal (1.99 g, 9.74 mmol, 1.5 equiv.), 1.07 g (44%) of the title compound as a light yellow oil was obtained after purification by flash chromatography on SiO2 (cyclohexane/EtOAc 997:3).

Sources & evidence

ORD record: ord-d4384ce46d1e4ac9bd0eabb3e58f8070
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193935B2

Reaction notes

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