HCID 21277002, compound → HCID 21277005, compound

HRID 2292218Notes

Reaction equation

HRID 2292218 reaction equation
[CH2:1]([Li])CCC.[CH3:6][O:7][C:8]1[C:9]([CH2:31][CH2:32][CH3:33])=[C:10]([CH:18]=[CH:19][C:20]=1[C:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][CH3:29])[O:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[N:17]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.CCCCCC>[CH3:6][O:7][C:8]1[C:9]([CH2:31][CH2:32][CH3:33])=[C:10]([CH:18]=[CH:19][C:20]=1[C:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][CH3:29])=[CH2:1])[O:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[N:17]

Participants

6

Reactant 2

HCID 21277002HCID 21277002, compoundHCID 178418339Butyllithium

Product 1

HCID 21277005HCID 21277005, compound

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a suspension of 0.56 g of methyltriphenylphosphonium bromide in 10 ml of dry tetrahydrofuran were added 0.88 ml of a 1.6 molar n-butyllithium solution in hexane. After stirring for 3 hours under a nitrogen atmosphere, 0.5 g of 5-[3-methoxy-4-(2-methoxybenzoyl)-2-propylphenoxy]pentanenitrile were added in 5 ml of tetrahydrofuran. The reaction was stirred for 40 hours at 25° C. and then at 65° C. for 24 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was evaporated to dryness. The residue was purified by preparative thin layer chromatography using a solvent system of 10% ethyl acetate in hexane. The appropriate band was isolated, extracted with ethyl acetate, dried over sodium sulfate, and evaporated in vacuo providing 50 mg of the desired title product as an oil.

Workup

  1. stirringThe reaction was stirred for 40 hours at 25° C.
  2. waitat 65° C. for 24 hours
  3. filtrationthe reaction mixture was filtered
  4. customthe filtrate was evaporated to dryness
  5. customThe residue was purified by preparative thin layer chromatography
  6. customThe appropriate band was isolated
  7. extractionextracted with ethyl acetate
  8. dry with materialdried over sodium sulfate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-3e41952426a9497eb04c465b27c2548f
Source dataset
uspto-grants-1989_01
Patent number
US04801616

Reaction notes

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