Cyclohexanecarboxaldehyde → HCID 178519912, compound

HRID 423197Notes

Reaction equation

HRID 423197 reaction equation
O1CCCCC1[O:7][CH2:8][C:9]1[CH:23]=[CH:22][C:12]([C:13]([CH2:15][C:16](=[O:21])[C:17]([O:19]C)=O)=[O:14])=[CH:11][CH:10]=1.[O:24]1[CH:28]=[CH:27][C:26]([C:29]2[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=2)=[N:25]1.[CH:36]1([CH:42]=O)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>O.C1COCC1.CO.C(O)(=O)C>[CH:36]1([CH:42]2[N:33]([C:32]3[CH:34]=[CH:35][C:29]([C:26]4[CH:27]=[CH:28][O:24][N:25]=4)=[CH:30][CH:31]=3)[C:17](=[O:19])[C:16]([OH:21])=[C:15]2[C:13](=[O:14])[C:12]2[CH:11]=[CH:10][C:9]([CH2:8][OH:7])=[CH:23][CH:22]=2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

9

Reactant 4

HCID 16275CyclohexanecarboxaldehydeHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 231185764-(1,2-Oxazol-3-yl)anilineHCID 58045028HCID 58045028, compound

Product 1

HCID 178519912HCID 178519912, compoundYield 9.1%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
95 °C

Procedure

To a mixture of methyl 4-(2-tetrahydro-2H-pyranoxy methyl)benzoyl-pyruvate (0.17 g, 0.53 mmol), 4-isoxazol-3-ylaniline (0.085 g, 0.53 mmol) and acetic acid (1 mL), cyclohexane carboaldehyde (0.064 mL, 0.53 mmol) was added. The mixture was stirred at 95° C. for 0.5 hr, and cooled to r.t. The precipitate was collected by filtration and washed with ethyl acetate to give crude precursor. Methanol (5 mL), THF (5 mL) and pyridinium p-toluenesulfonate (0.027 g, 0.11 mmol) were added to the precursor, and the mixture was stirred at 60° C. for 0.5 hr. Water was added to the mixture, which was then extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give 5-cyclohexyl-3-hydroxy-4-(4-hydroxy methylbenzoyl)-1-(4-isoxazol-3-yl-phenyl)-1,5-dihydropyrrol-2-one (0.022 g, 9%) as colorless crystals.

Workup

  1. additionwas added
  2. temperaturecooled to r.t
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with ethyl acetate
  5. customto give crude precursor
  6. stirringthe mixture was stirred at 60° C. for 0.5 hr
  7. extractionwas then extracted with chloroform
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-00fbe650ff214afdac23c413d1f96f1a
Source dataset
uspto-grants-2012_01
Patent number
US08101644B2

Reaction notes

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