3-Phenylpropyl triphenylphosphonium bromide → HCID 178420255, compound

HRID 1067728Notes

Reaction equation

HRID 1067728 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)N2C=C(CCC=O)N=C2)C=CC=CC=1.[Br-].C1(CCC[P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH:58]1[CH:62]=[C:61]([CH2:63][CH2:64][CH:65]=[CH:66][CH2:67][CH2:68][C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[N:60]=[CH:59]1>>[NH:58]1[CH:62]=[C:61]([CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][C:69]2[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=2)[N:60]=[CH:59]1

Participants

4

Reactant 3

HCID 109286473-Phenylpropyl triphenylphosphonium bromideHCID 114514283-(1-Tritylimidazol-4-YL) propionaldehydeHCID 1784413551-(1H-imidazol-4-yl)-6-phenyl-3-hexene

Product 1

HCID 178420255HCID 178420255, compound

Procedure

5 mmol of 3-(1-triphenylmethyl-1H-imidazol-4-yl)propanal (prepared according to standard methods (Swern oxidation) with 3-(1-triphenylmethyl-1H-imidazol-4-yl)propanol and oxalyl chloride in DMSO at −45° C.) and 5 mmol of 3-phenylpropyltriphenylphosphonium bromide (prepared from triphenylphosphine and 3-phenylpropyl bromide in toluene under reflux for 12 h) are treated as described in Example 51. The 1-(1H-imidazol-4-yl)-6-phenyl-3-hexene is hydrogenated as described in Example 52. The title compound is crystallized in the form of hydrogen oxalate in ethanol and diethyl ether.

Workup

  1. customThe title compound is crystallized in the form of hydrogen oxalate in ethanol and diethyl ether

Sources & evidence

ORD record
ord-676be74bc7e44b5180c7bf5a52abc00b
Source dataset
uspto-grants-2001_06
Patent number
US06248765B1

Reaction notes

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