Diethyl Ether → 2-methyl-6-[1-(1-trityl-1H-imidazol-4-yl)-vinyl]-pyridine

HRID 748648Notes

Reaction equation

[Br-].[CH3:2]P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Li]CCCC.[CH3:27][C:28]1[N:33]=[C:32]([C:34]([C:36]2[N:37]=[CH:38][N:39]([C:41]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH:40]=2)=O)[CH:31]=[CH:30][CH:29]=1.CCOCC>C1COCC1>[CH3:27][C:28]1[CH:29]=[CH:30][CH:31]=[C:32]([C:34]([C:36]2[N:37]=[CH:38][N:39]([C:41]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH:40]=2)=[CH2:2])[N:33]=1

Participants

Conditions

Temperature: -50 °C

Procedure

Methyl triphenylphosphine bromide (commercially available from Aldrich) (2.2 g, 6.16, mmol) in THF(60 mL) at −70° C. was treated with nBuLi (2.44 mL, 2.5M in hexane). The reaction mixture warmed to −50° C. in 1 h. A solution of (6-methyl-pyridin-2-yl)-(1-trityl-1H-imidazol-4-yl)-methanone (Intermediate D3) (1.38 g, 3.2 mmol) in THF (25 mL) was added to the mixture via syringe at −50° C. The mixture was allowed to warm to rt for 1.5 h. The mixture was poured into ether (mL) and washed with water (2×10 mL). The organic solution was dried over MgSO4, filtered and evaporated to leave a residue. This was purified by chromatography on SiO2 with diethyl ether to give 2-methyl-6-[1-(1-trityl-1H-imidazol-4-yl)-vinyl]-pyridine (Intermediate D4) 0.68 g (50%).

Workup

temperatureto warm to rt for 1.5 h
washwashed with water (2×10 mL)
dry with materialThe organic solution was dried over MgSO4
filtrationfiltered
customevaporated
customto leave a residue
customThis was purified by chromatography on SiO2 with diethyl ether

Sources & evidence

ORD record: ord-fb945cb59f904540a8c2b640b2a65913
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07399868B2

Reaction notes

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