2-Methylundecanal → HCID 86702787, compound

HRID 718549Notes

Reaction equation

[Br-].[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH:12]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:13].[Li]CCCC.[CH3:38][CH:39]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH:40]=O>>[CH3:40][CH:39]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH:38]=[C:12]([C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:2]=1)[CH3:13]

Participants

Reactant 3

HCID 610312-Methylundecanal

HCID 198421791-(2-Naphthyl)ethyltriphenylphosphonium bromide

HCID 178418339Butyllithium

Product 1

HCID 86702787HCID 86702787, compoundYield 23%

Conditions

Temperature: 25 °C

Procedure

Starting from (1-(2-naphthyl)ethyltriphenylphosphonium bromide (6.40 g, 12.9 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 8.0 mL, 12.9 mmol, 1.0 equiv.) and 2-methylundecanal (3.56 g, 19.3 mmol, 1.5 equiv.), and after stirring the mixture at 25° C. for 3 h, 0.94 g (23%) of the title compound as a colorless oil was obtained after purification by flash chromatography on SiO2 (cyclohexane).

Sources & evidence

ORD record: ord-5e0707dc53ca4443b75a459b50fdb9f0
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193935B2

Reaction notes

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