Triethyl 2-phosphonopropionate → HCID 54552716, compound

HRID 280224Notes

Reaction equation

HRID 280224 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:42]=[CH:41][C:29]([CH2:30][CH2:31][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]([CH2:30][CH2:31][C:32]2[N:37]3[CH:38]=[N:39][CH:40]=[C:36]3[CH:35]=[CH:34][CH:33]=2)=[CH:41][CH:42]=1)=[O:5])[CH3:1]

Participants

5

Reactant 3

HCID 107155Triethyl 2-phosphonopropionateHCID 2724682Lithium diisopropylamideHCID 23321866HCID 23321866, compound

Product 1

HCID 54552716HCID 54552716, 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 dry tetrahydrofuran at 0° under nitrogen. After stirring at 0° for 15 minutes 5-(p-formylphenethyl)-imidazo[1,5-a]pyridine (0.55 g) is added in 5 ml of tetrahydrofuran and the reaction mixture is stirred for 1 hour at 0° and 1 hour at 25° before quenching with 25 ml of water. The layers are separated and the organic phase is dried and evaporated. The resulting oil is redissolved in ethyl acetate and passed through a column of silica gel to remove the excess phosphonate and to yield 5-[p-(2-ethoxycarbonylprop-1-enyl)phenethyl]imidazo[1,5-a]pyridine.

Workup

  1. custombefore quenching with 25 ml of water
  2. customThe layers are separated
  3. customthe organic phase is dried
  4. customevaporated
  5. dissolutionThe resulting oil is redissolved in ethyl acetate
  6. customto remove the excess phosphonate

Sources & evidence

ORD record
ord-fdcc4f27f7784965965103db6e63aa4d
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

Loading…