2-Chlorobenzaldehyde → 4-[2-(2-chloro-phenyl)-vinyl]-1-trityl-1H-imidazole

HRID 1946963Notes

Reaction equation

C(OP([CH2:9][C:10]1[N:11]=[CH:12][N:13]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=1)(=O)OCC)C.CC([O-])(C)C.[K+].[Cl:40][C:41]1[CH:48]=[CH:47][CH:46]=[CH:45][C:42]=1[CH:43]=O>C1COCC1>[Cl:40][C:41]1[CH:48]=[CH:47][CH:46]=[CH:45][C:42]=1[CH:43]=[CH:9][C:10]1[N:11]=[CH:12][N:13]([C:15]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:14]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred suspension of (1-trityl-1H-imidazol-4-ylmethyl)-phosphonic acid diethyl ester (448 mg; CAS 473659-21-1) at r.t. in THF (7 ml) under an argon atmosphere were added potassium tert-butylate (109 mg) and 2-chlorobenzaldehyde (114 mg). The mixture (clear brown orange solution) was heated to 80° C. over night. The reaction mixture was cooled to r.t and concentrated. The crude product was purified by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 3:2) to give 4-[2-(2-chloro-phenyl)-vinyl]-1-trityl-1H-imidazole (329 mg) as off-white solid. MS (ISP): 243.3 ([Trt]+)

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated
customThe crude product was purified by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 3:2)

Sources & evidence

ORD record: ord-ee8790c8d34743bd985ae12767793829
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399463B2

Reaction notes

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