4-Methoxybenzaldehyde → HCID 57041857, compound

HRID 718522Notes

Reaction equation

HRID 718522 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][O:35][C:36]1[CH:43]=[CH:42][C:39]([CH:40]=O)=[CH:38][CH:37]=1>>[CH3:34][O:35][C:36]1[CH:43]=[CH:42][C:39]([CH:40]=[CH:2][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:38][CH:37]=1

Participants

4

Reactant 3

HCID 312444-MethoxybenzaldehydeHCID 10863251Phenethyltriphenylphosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 57041857HCID 57041857, compoundYield 86%

Procedure

Starting from phenethyltriphenylphosphonium bromide (3.16 g, 7.06 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 4.4 mL, 7.06 mmol, 1.0 equiv.) and 4-methoxybenzaldehyde (1.44 g, 10.6 mmol, 1.5 equiv.), 1.36 g (86%) of the title compound as a light yellow oil was obtained after purification by flash chromatography on SiO2 (cyclohexane/EtOAc 99:1).

Sources & evidence

ORD record
ord-321a2ed87eab4629bfbcf625ff6cf728
Source dataset
uspto-grants-2015_11
Patent number
US09193935B2

Reaction notes

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