Acetic Acid → Cyclobutylmethyl 2-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]-3-oxobutanoate

HRID 1669788Notes

Reaction equation

HRID 1669788 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=O.[O:15]=[C:16]([CH3:26])[CH2:17][C:18]([O:20][CH2:21][CH:22]1[CH2:25][CH2:24][CH2:23]1)=[O:19].C(O)(=O)C.N1CCCCC1>ClCCl>[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=[C:17]([C:16](=[O:15])[CH3:26])[C:18]([O:20][CH2:21][CH:22]1[CH2:25][CH2:24][CH2:23]1)=[O:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 57438895Cyclobutylmethyl 3-oxobutanoate

Product 1

HCID 66991437Cyclobutylmethyl 2-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

700 mg (3.72 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde, 760 mg (4.46 mmol) of cyclobutylmethyl 3-oxobutanoate, 53 μl (0.93 mmol) of acetic acid and 92 μl (0.93 mmol) of piperidine in 25 ml of anhydrous dichloromethane are heated after addition of 4 Å molecular sieves (1.5 g) under reflux for 24 h. After cooling, the suspension is filtered with suction and the filtrate is washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated. The residue is purified by preparative HPLC. 962 mg (76% of theory) of the title compound are obtained as an E/Z mixture.

Workup

  1. additionafter addition of 4 Å molecular sieves (1.5 g)
  2. temperatureunder reflux for 24 h
  3. temperatureAfter cooling
  4. filtrationthe suspension is filtered with suction
  5. washthe filtrate is washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-c944024e3522476c968abf9223c5717a
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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