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

HRID 557433Notes

Reaction equation

HRID 557433 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 under reflux after addition of 4 Å molecular sieves (1.5 g) for 24 h. After cooling, the suspension is filtered with suction and the filtrate is washed successively with saturated sodium bicarbonate solution and 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. temperatureunder reflux
  2. additionafter addition of 4 Å molecular sieves (1.5 g) 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 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-9ef0f3e6c56e4be58a678ddb44986b6a
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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