Acetic Acid → 3-Oxo-2-[(9-oxo-9H-fluoren-4-yl)methylene]butanenitrile

HRID 1951379Notes

Reaction equation

HRID 1951379 reaction equation
[C:1]([CH:3]=[C:4]([O-:6])[CH3:5])#[N:2].[Na+].[O:8]=[C:9]1[C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:22]=O)[C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2.C(O)(=O)C.N1CCCCC1>ClCCl>[O:6]=[C:4]([CH3:5])[C:3](=[CH:22][C:17]1[C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:8])[C:21]=2[CH:20]=[CH:19][CH:18]=1)[C:1]#[N:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 113332519-Oxo-9H-fluorene-4-carbaldehydeHCID 74083625Sodium 1-cyanoprop-1-en-2-olate

Product 1

HCID 674179733-Oxo-2-[(9-oxo-9H-fluoren-4-yl)methylene]butanenitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The compound from example 11A (5.21 g, 25.0 mmol) is introduced into 180 ml of dichloromethane, and the compound from example 20A (2.89 g, 27.5 mmol), acetic acid (1.72 ml, 30.0 mmol) and piperidine (0.25 ml, 2.50 mmol) are added. The mixture is stirred at the boiling point with a water trap for 4 h. Cooling to RT is followed by dilution with 30 ml of dichloromethane and washing with water (2×50 ml), the organic phase is dried over sodium sulfate and the solvent is removed in a rotary evaporator. The resulting crude product is purified by chromatography on silica gel 60 with dichloromethane as mobile phase. Combining the product fractions and removing the solvent results in 5.40 g (79% of theory) of the title compound as mixture of E/Z isomers.

Workup

  1. washwashing with water (2×50 ml)
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. customthe solvent is removed in a rotary evaporator
  4. customThe resulting crude product is purified by chromatography on silica gel 60 with dichloromethane as mobile phase
  5. customremoving the solvent

Sources & evidence

ORD record
ord-bdae7f54926e42d1a67f1fdf84f4d451
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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