3-(4-Ethylphenyl)-2,2-dimethylpropanal → HCID 86702770, compound

HRID 718524Notes

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.[CH2:34]([C:36]1[CH:41]=[CH:40][C:39]([CH2:42][C:43]([CH3:47])([CH3:46])[CH:44]=O)=[CH:38][CH:37]=1)[CH3:35]>>[CH3:44][C:43]([CH3:46])([CH:47]=[CH:2][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:42][C:39]1[CH:38]=[CH:37][C:36]([CH2:34][CH3:35])=[CH:41][CH:40]=1

Participants

Reactant 3

HCID 1055133-(4-Ethylphenyl)-2,2-dimethylpropanal

HCID 10863251Phenethyltriphenylphosphonium bromide

HCID 178418339Butyllithium

Product 1

HCID 86702770HCID 86702770, compoundYield 51.2%

Procedure

Starting from phenethyltriphenylphosphonium bromide (2.23 g, 4.98 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 3.1 mL, 4.98 mmol, 1.0 equiv.) and 3-(4-ethylphenyl)-2,2-dimethylpropanal (1.42 g, 7.48 mmol, 1.5 equiv.), 0.71 g (51%) 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-7517a7d539e14e13b83bea8e640fd853
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193935B2

Reaction notes

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