Water → HCID 59694095, compound

HRID 735728Notes

Reaction equation

HRID 735728 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH:17]([C:19]1[N:20]([C:24]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:21]=[CH:22][N:23]=1)=O.O>O1CCCC1>[C:24]([N:20]1[CH:21]=[CH:22][N:23]=[C:19]1/[CH:17]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 6182531-(triphenylmethyl)-1H-imidazole-2-carbaldehyde

Product 1

HCID 59694095HCID 59694095, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (60% in oil, 0.811 g, 20.3 mmol) in tetrahydrofuran (60 ml) was added dropwise ethyl (diethoxyphosphoryl)acetate (4.33 ml, 21.8 mmol) and the mixture was stirred for 30 min. A solution of 2-formyl-1-tritylimidazole (5.28 g, 15.6 mmol) in tetrahydrofuran (30 ml) was added dropwise and the mixture was stirred for 8 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried (over anhydrous MgSO4). After concentration under reduced pressure, the obtained residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (9:1-1:1, v/v). The title compound (3.28 g, 52%) was obtained as a colorless powder from the object fraction.

Workup

  1. stirringthe mixture was stirred for 8 hrs
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried (over anhydrous MgSO4)
  5. concentrationAfter concentration under reduced pressure
  6. washeluted with hexane-ethyl acetate (9:1-1:1

Sources & evidence

ORD record
ord-8fe74c2942634af8aa2846d917c5a10e
Source dataset
uspto-grants-2009_09
Patent number
US07592453B2

Reaction notes

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