Lithium diisopropylamide → HCID 54218001, compound

HRID 485349Notes

Reaction equation

HRID 485349 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH3:9][CH2:10][O:11][C:12](/[CH:14]=[CH:15]/[CH2:16]P(OCC)(OCC)=O)=[O:13].[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([N:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=[C:32]2[CH:40]=O)[CH:26]=1>O1CCCC1>[CH2:10]([O:11][C:12]([CH:14]=[CH:15][CH:16]=[CH:40][C:32]1[N:31]([C:27]2[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=2)[C:39]2[C:34]([CH:33]=1)=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:13])[CH3:9]

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomersHCID 13490360HCID 13490360, compound

Product 1

HCID 54218001HCID 54218001, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium diisopropylamide (from 0.57 ml of diisopropylamine and 2.5 ml of 1.6M n-butyllithium in hexane) in 20 ml of dry tetrahydrofuran under nitrogen is cooled to -70° and 0.78 ml of triethyl 4-phosphonocrotonate is added dropwise. The reaction mixture is stirred for 30 minutes at -70°, and then a solution of 0.9 g of N-(3-pyridyl)indole-2-carboxaldehyde in 5 ml of tetrahydrofuran is added slowly. The reaction mixture is allowed to warm to room temperature, is stirred for 14 hours and is evaporated to an oil which is partitioned between 15 ml of half-saturated ammonium chloride solution and 40 ml of ethyl ether. The organic phase is washed with 10 ml of water, dried over sodium sulfate and evaporated to yield 2-[4-(ethoxycarbonyl)butadienyl]-N-(3-pyridyl)indole as a waxy solid; Rf (10% methanol and toluene, silica gel)=0.7.

Workup

  1. stirringis stirred for 14 hours
  2. customis evaporated to an oil which
  3. customis partitioned between 15 ml of half-saturated ammonium chloride solution and 40 ml of ethyl ether
  4. washThe organic phase is washed with 10 ml of water
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-d009083e2ad0431ab425db573a0268e0
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

Loading…