Benzaldehyde → HCID 54699181, compound

HRID 1650817Notes

Reaction equation

HRID 1650817 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH3:9][N:10]1[CH2:14][C:13]([OH:15])=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:17]=2)[C:11]1=[O:35].[CH:36](=O)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[Cl-].[NH4+].[O:46]1CCCC1>>[CH3:9][N:10]1[C:14]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([OH:46])[C:13]([OH:15])=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:17]=2)[C:11]1=[O:35]

Participants

6

Reactant 5

HCID 240BenzaldehydeHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 546991822H-Pyrrol-2-one, 1,5-dihydro-3-(3-(dodecyloxy)phenyl)-4-hydroxy-1-methyl-

Product 1

HCID 54699181HCID 54699181, compound

Conditions

Temperature
0 °C

Procedure

To the solution of lithium diisopropylamide (1.1 m mol) in tetrahydrofuran (16 ml) was added N-methyl-3-(3-dodecyloxyphenyl)-4-hydroxy-3-pyrrolin-2-one (0.19 g, 0.5 m mol) at -78° C. and the mixture was stirred for 5 minutes at 0° C. The reaction mixture was cooled to -78° C. and, to this, was added benzaldehyde (0.15 ml, 1.5 m mol), stirring for 30 minutes. A saturated aqueous ammonium chloride solution (20 ml) was added to the reaction mixture and the resultant mixture was extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (developing solvent: ethyl acetate:hexane=1:1) to obtain two diastereomers of N-methyl-3-(3-dodecyloxyphenyl)-4-hydroxy-5-hydroxy-(phenyl)methyl-3-pyrrolin-2-one [diastereomer A (5-j): 0.10 g, diastereomer B (5-k): 0.05 g]. The former was recrystallized from IPE to give crystals of m.p. 117°-118° C. and the latter was recrysrtallized from methanol to give crystals of m.p. 110°-111° C.

Workup

  1. temperatureThe reaction mixture was cooled to -78° C.
  2. stirringstirring for 30 minutes
  3. extractionthe resultant mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (developing solvent: ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-2c63e51b997447f1942e9dc02a376fdf
Source dataset
uspto-grants-1990_05
Patent number
US04925868

Reaction notes

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