2-Methylundecanal → HCID 86702759, compound

HRID 718509Notes

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][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH:36]=O>>[CH3:36][CH:35]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH:34]=[CH:2][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Reactant 3

HCID 610312-Methylundecanal

HCID 10863251Phenethyltriphenylphosphonium bromide

HCID 178418339Butyllithium

Product 1

HCID 86702759HCID 86702759, compoundYield 61%

Procedure

Starting from phenethyltriphenylphosphonium bromide (3.60 g, 8.05 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 5.0 mL, 8.05 mmol, 1.0 equiv.) and 2-methylundecanal (2.25 g, 12.1 mmol, 1.5 equiv.), 1.33 g (61%) of the title compound as a colorless oil was obtained after purification by flash chromatography on SiO2 (hexanes).

Sources & evidence

ORD record: ord-e48b22680c0c4224b7b1b85af21ebeff
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193935B2

Reaction notes

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