Ethanol → HCID 14551199, compound

HRID 1165898Notes

Reaction equation

HRID 1165898 reaction equation
C(=O)[CH2:2][CH:3]([CH3:5])[CH3:4].N1CCOCC1.C(O)C.[CH3:16][O:17][C:18]([C:20]1[C:24](=O)O[C:22]2=[CH:26][CH:27]=[C:28]([CH:31]([CH3:33])[CH3:32])[CH:29]=[CH:30][C:21]=12)=[O:19]>C1(C)C=CC=CC=1>[CH3:16][O:17][C:18]([C:20]1[C:21]2[C:22]([CH:26]=[CH:27][C:28]([CH:31]([CH3:33])[CH3:32])=[CH:29][CH:30]=2)=[C:2]([CH:3]([CH3:5])[CH3:4])[CH:24]=1)=[O:19]

Participants

6

Reactant 4

HCID 702EthanolHCID 8083MorpholineHCID 115523-MethylbutanalHCID 14515736HCID 14515736, compound

Product 1

HCID 14551199HCID 14551199, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Isovaleraldehyde (5.16 g) and morpholine (4.36 g) are added to ethanol (14 ml) and then 3-methoxycarbonyl-6-isopropyl-2H-cyclohepta[b]furan-2-one (5) (2.46 g) is added thereto. The obtained mixture is heated under reflux for 16 hours, and then the solvent is distilled off under reduced pressure to give an oily material. The obtained oily material is dissolved in toluene (20 ml), washed twice with water (20 ml) and 4 times with 1N HCl (20 ml), and further, twice with water (40 ml). The obtained toluene layer is passed through silica gel column (1.05 kg), the column is eluted with toluene. From the eluted parts including the product (24), the solvent is distilled off under reduced pressure to give the compound (24) as a purple oily material in a yield of 2.08 g, 76.%.

Workup

  1. temperatureThe obtained mixture is heated
  2. temperatureunder reflux for 16 hours
  3. distillationthe solvent is distilled off under reduced pressure
  4. customto give an oily material
  5. washwashed twice with water (20 ml) and 4 times with 1N HCl (20 ml)
  6. washthe column is eluted with toluene
  7. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-82945cad1443406f8f5976df7afb2267
Source dataset
uspto-grants-1990_03
Patent number
US04912134

Reaction notes

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