Methyl 3-(1-Tritylimidazol-4-yl) Propionate → 3-(1-Tritylimidazol-4-YL) propionaldehyde

HRID 478001

Reaction equation

HRID 478001 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([N:30]1[CH:34]=[C:33]([CH2:35][CH2:36][C:37](OC)=[O:38])[N: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)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1.C(Cl)Cl>[C:11]([N:30]1[CH:34]=[C:33]([CH2:35][CH2:36][CH:37]=[O:38])[N:32]=[CH:31]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

5

Reactant 2

HCID 10475868Methyl 3-(1-Tritylimidazol-4-yl) PropionateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 114514283-(1-Tritylimidazol-4-YL) propionaldehydeYield 50.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 44.4 mmole of diisobutylaluminium hydride in 29 ml of toluene is added to a solution of 8.79 g of methyl 3-(1-tritylimidazol-4-yl)propionate in 175 ml of methylene chloride at -72° under nitrogen. After 5 min the reaction is quenched by adding 14 ml of methanol followed by 90 ml of water. The reaction mixture is allowed to warm to room temperature and is filtered through celite. The organic phase is separated, dried over sodium sulfate and evaporated to a yellow oil which is chromatographed on 280 g of silica with ether to yield 4.13 g of 3-(1-tritylimidazol-4-yl)propionaldehyde as an oil. IR (CDCl3): 2830, 2740, 1730 cm-1.

Workup

  1. customAfter 5 min the reaction is quenched
  2. additionby adding 14 ml of methanol
  3. filtrationis filtered through celite
  4. customThe organic phase is separated
  5. dry with materialdried over sodium sulfate
  6. customevaporated to a yellow oil which
  7. customis chromatographed on 280 g of silica with ether

Sources & evidence

ORD record
ord-81de414de58e46f7a2c0bfbac14716a1
Source dataset
uspto-grants-1989_12
Patent number
US04889861

Linked notes

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