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

HRID 76878
Notes
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Reaction equation

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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1140TolueneHCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 10475868Methyl 3-(1-Tritylimidazol-4-yl) Propionate

Product 1

HCID 114514283-(1-Tritylimidazol-4-YL) propionaldehyde

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 6344DichloromethaneSolvent

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

  1. customThe mixture is partitioned between DCM and saturated aqueous Rochelle salt solution
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. customevaporated
  4. 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

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes