trans-4-Decen-1-al → HCID 86702766, compound

HRID 718519Notes

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

Participants

Reactant 3

HCID 5702654trans-4-Decen-1-al

HCID 10863251Phenethyltriphenylphosphonium bromide

HCID 178418339Butyllithium

Product 1

HCID 86702766HCID 86702766, compoundYield 62.3%

Procedure

Starting from phenethyltriphenylphosphonium bromide (3.20 g, 7.15 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 4.5 mL, 7.15 mmol, 1.0 equiv.) and (E)-dec-4-enal (1.66 g, 10.7 mmol, 1.5 equiv.), 1.08 g (62%) 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-f16ff84bbe7c4945a15a0539d5de2b39
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193935B2

Reaction notes

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