Trityl chloride → 1-(triphenylmethyl)-1H-imidazole-2-carbaldehyde

HRID 899735Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7].C(N(CC)C(C)C)(C)C.[C:17](Cl)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[C:17]([N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 30 °C

Procedure

To a suspension of imidazole-2-carboxaldehyde (1.00 g, 10.4 mmol) in DMF (16 mL) was added N,N-diisopropylethylamine (4.0 mL, 23.0 mmol) followed by a solution of trityl chloride (3.19 g, 11.4 mmol) in DMF (10 mL), and the mixture was stirred at 30° C. for 21 h. The mixture was concentrated in vacuo then dissolved in EtOAc (60 mL). The solution was washed with saturated NaHCO3(aq) (2×30 mL) and brine (15 mL) then dried (MgSO4) and concentrated in vacuo. Purification of the crude material by column chromatography on silica gel (20% EtOAc/hexanes) gave a yellow solid (1.63 g, 46%). 1H NMR (CDCl3) δ 7.03 (s, 1H), 7.12 (m, 6H), 7.32 (m, 10H), 9.23 (s, 1H).

Workup

concentrationThe mixture was concentrated in vacuo
dissolutionthen dissolved in EtOAc (60 mL)
washThe solution was washed with saturated NaHCO3(aq) (2×30 mL) and brine (15 mL)
dry with materialthen dried (MgSO4)
concentrationconcentrated in vacuo
customPurification of the crude material by column chromatography on silica gel (20% EtOAc/hexanes)

Sources & evidence

ORD record: ord-c04f34a66f114c85acc3808e4ead3c24
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07354934B2

Reaction notes

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