Ethyl Acetate → 1-[(Diphenylmethylene)amino]-5-methylpyrrolidin-2-one
Reaction equation
[H-].[Na+].Br[CH:4]([CH3:24])[CH2:5][CH2:6][C:7]([NH:9][N:10]=[C:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8].C(OCC)(=O)C>O1CCCC1>[C:12]1([C:11](=[N:10][N:9]2[CH:4]([CH3:24])[CH2:5][CH2:6][C:7]2=[O:8])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1Participants
Procedure
At 0° C., 2.7 g (68.0 mmol) of sodium hydride are added a little at a time to a solution of 33.0 g (68.0 mmol) of 4-bromo-N′-(diphenylmethylene)pentane hydrazide in 200 ml of tetrahydrofuran. The reaction mixture is stirred at room temperature for 16 h, and ethyl acetate/saturated aqueous NH4Cl solution is then added. The organic phase is separated off and the aqueous phase is extracted with 3×250 ml of ethyl acetate. The combined organic phases are dried over Na2SO4 and freed from the solvent under reduced pressure. Purification by column chromatography on silica gel (cyclohexane/ethyl acetate) gives 17.8 g (89%) of the desired product; log P(HCOOH): 2.73; 1H-NMR (ppm): δ (DMSO-d6)=1.22 (d, 3H), 2.05-2.15 (m, 4H), 3.86 (m, 1H), 7.24-7.26 (m, 2H), 7.40-7.43 (m, 4H), 7.48-7.53 (m, 4H); LC-MS: m/z=279 [M+H]+
Workup
- customThe organic phase is separated off
- extractionthe aqueous phase is extracted with 3×250 ml of ethyl acetate
- dry with materialThe combined organic phases are dried over Na2SO4
- customPurification by column chromatography on silica gel (cyclohexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-f949f509bcb54211a894203d048e0c9c
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507472B2
Reaction notes
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