trans-4-Decen-1-al → HCID 67982301, compound

HRID 718531Notes

Reaction equation

[Br-].[CH3:2][O:3][C:4]1[CH:30]=[CH:29][C:7]([CH2:8][CH2:9][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:6][CH:5]=1.[Li]CCCC.[CH:36](=O)[CH2:37][CH2:38]/[CH:39]=[CH:40]/[CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]>>[CH2:8]([C:7]1[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:30][CH:29]=1)[CH:9]=[CH:36][CH2:37][CH2:38]/[CH:39]=[CH:40]/[CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]

Participants

Reactant 3

HCID 5702654trans-4-Decen-1-al

HCID 85891800p-Methoxyphenethyltriphenylphosphonium bromide

HCID 178418339Butyllithium

Product 1

HCID 67982301HCID 67982301, compoundYield 48%

Procedure

Starting from p-methoxyphenethyltriphenylphosphonium bromide (3.12 g, 6.54 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 4.1 mL, 6.54 mmol, 1.0 equiv.) and (E)-dec-4-enal (1.51 g, 9.80 mmol, 1.5 equiv.), 0.85 g (48%) of the title compound as a colorless oil was obtained after purification by flash chromatography on SiO2 (hexanes/EtOAc 992:8).

Sources & evidence

ORD record: ord-3eaef145e03f46b59b5eb262808464ac
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193935B2

Reaction notes

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