Tetrahydrofuran → HCID 22503442, compound

HRID 1006954Notes

Reaction equation

HRID 1006954 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O1CC[CH2:19][CH2:18]1>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C>[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([C:18]#[CH:19])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 192201-Benzyl-4-piperidoneHCID 24758Sodium hydride

Product 1

HCID 22503442HCID 22503442, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)Catalyst

Procedure

Ethyl triphenylphosphonium bromide (25 g) was suspended in tetrahydrofuran (100 ml), followed by the addition of 60% sodium hydride (2.68 g) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. The reaction solution was ice-cooled again, followed by the addition of 1-benzyl-4-piperidone (11.55 g), and the resulting mixture was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a colorless oil (6.08 g, yield; 52%).

Workup

  1. temperaturecooling
  2. temperaturecooled again
  3. stirringthe resulting mixture was stirred at room temperature overnight
  4. customThe reaction mixture was partitioned between ethyl acetate and water
  5. washThe resulting organic layer was washed with water
  6. dry with materialdried (over MgSO4)
  7. customevaporated
  8. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-b87f3b5829a04dd29c1fb690ef916e6f
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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