Toluene → 3-(1-Tritylimidazol-4-YL) propionaldehyde

HRID 76878

Reaction equation

C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[N:7]=[CH:8][N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1.C1(C)C=CC=CC=1.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(Cl)Cl.CO>[C:11]([N:9]1[CH:10]=[C:6]([CH2:5][CH2:4][CH:3]=[O:2])[N:7]=[CH:8]1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: -78 °C

Procedure

3-(1-Trityl-1H-imidazol-4-yl)propionic acid methyl ester (7.75 g, 19.5 mmol), J. Org. Chem. 2000, 65, 2229-2230, is dissolved in DCM (300 mL) and cooled to −78° C. To this is added a toluene solution of DIBAL (21.0 mL, 1.5 M). After 2 h MeOH (20 mL) is added followed by saturated aqueous Rochelle salt solution (50 mL). The mixture is partitioned between DCM and saturated aqueous Rochelle salt solution. The organic phase is dried (Na2SO4) and evaporated. The crude residue is purified via flash column chromatography (MeOH/DCM 1:99→MeOH/DCM 5:95) to give the aldehyde, 3-(1-trityl-1H-imidazol-4-yl)propionaldehyde as a yellow gum (cas #184030-88-4). 1H NMR (CDCl3) δ 9.83 (s, 1H), 7.38-7.31 (m, 10H), 7.16-7.12 (m, 6H), 6.58 (s, 1H), 2.90 (t, J=8.0 Hz, 2H), 2.83-2.79 (m, 2H).

Workup

customThe mixture is partitioned between DCM and saturated aqueous Rochelle salt solution
dry with materialThe organic phase is dried (Na2SO4)
customevaporated
customThe crude residue is purified via flash column chromatography (MeOH/DCM 1:99→MeOH/DCM 5:95)

Sources & evidence

ORD record: ord-be1999ba89174bc396a9555d08f6c297
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835646B2

Linked notes

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