Triethyl 2-phosphonopropionate → HCID 54386781, compound

HRID 280218Notes

Reaction equation

HRID 280218 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6](P(OCC)(OCC)=O)[CH3:7])=[O:5].C([N-]C(C)C)(C)C.[Li+].[CH:24]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[N:37]3[CH:38]=[N:39][CH:40]=[C:36]3[CH:35]=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)=O>O1CCCC1>[CH2:2]([O:3][C:4]([C:6]([CH3:7])=[CH:24][C:26]1[CH:27]=[CH:28][C:29]([C:32]2[N:37]3[CH:38]=[N:39][CH:40]=[C:36]3[CH:35]=[CH:34][CH:33]=2)=[CH:30][CH:31]=1)=[O:5])[CH3:1]

Participants

5

Reactant 3

HCID 107155Triethyl 2-phosphonopropionateHCID 2724682Lithium diisopropylamideHCID 136494335-(p-Formylphenyl)-imidazo[1,5-a]pyridine

Product 1

HCID 54386781HCID 54386781, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Triethyl 2-phosphonopropionate (0.61 g) is added to a solution of lithium diisopropylamide (from 0.32 g of diisopropylamine and 1.7 ml of 1.64M n-butyllithium) in 20 ml of tetrahydrofuran at 0° under nitrogen. After stirring for 10 minutes, 5-(p-formylphenyl)-imidazo[1,5-a]pyridine (0.50 g) is added dropwise in a solution of 5 ml of tetrahydrofuran. The reaction mixture is stirred for two hours at 0° and quenched with 25 ml of water. The layers are separated and aqueous phase is extracted with ethyl acetate (2×10 ml). The organic phases are combined, dried over sodium sulfate, filtered and evaporated to yield an oil which is chromatographed on silica gel with ethyl acetate as eluent to yield 5-[p-(2-ethoxycarbonylprop-1-enyl)phenyl]imidazo[1,5-a]pyridine; IR (CH2Cl2) 1700 cm-1.

Workup

  1. stirringThe reaction mixture is stirred for two hours at 0°
  2. customquenched with 25 ml of water
  3. customThe layers are separated
  4. extractionaqueous phase is extracted with ethyl acetate (2×10 ml)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto yield an oil which
  9. customis chromatographed on silica gel with ethyl acetate as eluent

Sources & evidence

ORD record
ord-8d093c0643ed49518a48800d6d67bb1d
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

Loading…