Sodium hydride → HCID 12953545, compound

HRID 614272Notes

Reaction equation

HRID 614272 reaction equation
[C:1]1([C:7]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:11]([CH2:12][NH:13][CH:14]([CH3:16])[CH3:15])[CH2:10][O:9][C:8]2=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+]>C(CC(C)(C)C)(C)C>[C:18]1([C:7]2([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:11]([CH2:10][OH:9])[CH2:12][N:13]([CH:14]([CH3:15])[CH3:16])[C:8]2=[O:17])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 24758Sodium hydride2×HCID 12953543HCID 12953543, compound

Product 1

HCID 12953545HCID 12953545, compound

Reagents, catalysts & solvents 1

HCID 109072,2,4-TrimethylpentaneSolvent

Procedure

Fifty-three grams (0.17 mole) of 4,5-dihydro-3,3-diphenyl-4-isopropylaminomethylfuran-2-(3H)one was dissolved in 300 ml. of boiling isooctane and 0.25 g. of 67% sodium hydride added. After refluxing for 6.5 hours an additional 0.25 g. of 57% sodium hydride was added and refluxing was continued overnight. The cooled mixture was filtered and the solid was recrystallized from toluene. The 3,3-diphenyl-4-hydroxymethyl-1-isopropyl-2-pyrrolidinone weighed 42 g. (80%) and melted at 159°-161° C. Analysis: Calcd. for C20H23NO2 : C, 77.64; H, 7.49; N, 4.53. Found: C, 77.71; H, 7.52; N, 4.37.

Workup

  1. temperatureAfter refluxing for 6.5 hours an additional 0.25 g
  2. temperaturerefluxing
  3. filtrationThe cooled mixture was filtered
  4. customthe solid was recrystallized from toluene

Sources & evidence

ORD record
ord-5177312df78342b6b5b93c7dd8d23d27
Source dataset
uspto-grants-1979_03
Patent number
US04144245

Reaction notes

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