Phenethyltriphenylphosphonium bromide → HCID 86702772, compound

HRID 718526Notes

Reaction equation

HRID 718526 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.[C:34]([CH:38]1[CH2:43][CH2:42][CH2:41][CH:40]([CH2:44][CH2:45][CH:46]=O)[CH2:39]1)([CH3:37])([CH3:36])[CH3:35]>>[C:34]([CH:38]1[CH2:43][CH2:42][CH2:41][CH:40]([CH2:44][CH2:45][CH:46]=[CH:2][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:39]1)([CH3:37])([CH3:36])[CH3:35]

Participants

4

Reactant 3

HCID 10863251Phenethyltriphenylphosphonium bromideHCID 57429401HCID 57429401, compoundHCID 178418339Butyllithium

Product 1

HCID 86702772HCID 86702772, compoundYield 61.1%

Procedure

Starting from phenethyltriphenylphosphonium bromide (2.60 g, 5.81 mmol, 1.0 equiv.), n-BuLi (1.3 M in hexanes, 4.5 mL, 5.81 mmol, 1.0 equiv.) and 3-(3-tert-butylcyclohexyl)propanal (1.45 g, 7.39 mmol, 1.3 equiv.), 1.01 g (61%) of the title compound as a colorless oil was obtained after purification by flash chromatography on SiO2 (cyclohexane).

Sources & evidence

ORD record
ord-f660562352cb43eeadb1fe4efb3dec68
Source dataset
uspto-grants-2015_11
Patent number
US09193935B2

Reaction notes

Loading…