trans-4-Decen-1-al → HCID 86702776, compound

HRID 718535Notes

Reaction equation

HRID 718535 reaction equation
[Br-].[CH3:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][CH2:8][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.[Li]CCCC.[CH:35](=O)[CH2:36][CH2:37]/[CH:38]=[CH:39]/[CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]>>[CH2:7]([C:6]1[CH:5]=[CH:4][C:3]([CH3:2])=[CH:29][CH:28]=1)[CH:8]=[CH:35][CH2:36][CH2:37]/[CH:38]=[CH:39]/[CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Participants

4

Reactant 3

HCID 5702654trans-4-Decen-1-alHCID 20466351(2-(P-Tolyl)ethyl)triphenylphosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 86702776HCID 86702776, compoundYield 57%

Procedure

Starting from p-methylphenethyltriphenylphosphonium bromide (2.90 g, 6.29 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 3.9 mL, 6.29 mmol, 1.0 equiv.) and (E)-dec-4-enal (1.45 g, 9.43 mmol, 1.5 equiv.), 0.92 g (57%) 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-9def2371bf404502974f068bd00ed14b
Source dataset
uspto-grants-2015_11
Patent number
US09193935B2

Reaction notes

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