Acetic Acid → HCID 86746325, compound

HRID 373384Notes

Reaction equation

HRID 373384 reaction equation
C(O)(=O)C.N1CCCC1.[CH3:10][C:11]([CH3:13])=[O:12].[F:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([C:32]2[C:37]([OH:38])=[C:36]([CH3:39])[C:35]([CH3:40])=[C:34]([CH:41]=O)[C:33]=2[CH3:43])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:17][CH:16]=1>O>[F:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([C:32]2[C:33]([CH3:43])=[C:34]([CH:41]=[CH:10][C:11](=[O:12])[CH3:13])[C:35]([CH3:40])=[C:36]([CH3:39])[C:37]=2[OH:38])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 31268PyrrolidineHCID 15125141HCID 15125141, compound

Product 1

HCID 86746325HCID 86746325, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To acetic acid (0.14 ml) were added pyrrolidine (0.2 ml) and acetone (0.26 ml). To this solution was added ethyl 7-(4-fluorophenyl)-7-(3-formyl-6-hydroxy-2,4,5-trimethylphenyl)heptanoate (1.0 g) and the mixture was stirred for 6.5 hours. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain ethyl 7-(4-fluorophenyl)-7-[2-hydroxy-5-(3-oxobutenyl)-3,4,6-trimethylphenyl]heptanoate (0.95 g) (Compound 42). The physical properties and spectrum data thereof are shown in Tables 3 and 4.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated saline
  3. dry with materialdried with anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-71d67566ea57409bbc60f0c64239a5fa
Source dataset
uspto-grants-1992_11
Patent number
US05162571

Reaction notes

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