1,3-Dimethyl-2-imidazolidinone → 1-[[3-(2-Hydroxyethyl)phenyl]methyl]cyclopentanecarbonitrile

HRID 274128Notes

Reaction equation

HRID 274128 reaction equation
C(NC(C)C)(C)C.[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].[CH:13]1([C:18]#[N:19])[CH2:17][CH2:16][CH2:15][CH2:14]1.CN1CCN(C)C1=[O:27].[CH3:28][CH2:29][CH2:30][CH2:31][CH2:32]C>O1CCCC1>[OH:27][CH2:8][CH2:9][C:10]1[CH:11]=[C:31]([CH2:32][C:13]2([C:18]#[N:19])[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 5

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 7912DiisopropylamineHCID 8058HexaneHCID 77935CyclopentanecarbonitrileHCID 178418339Butyllithium

Product 1

HCID 189994741-[[3-(2-Hydroxyethyl)phenyl]methyl]cyclopentanecarbonitrileYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Obtained by operating as in example 87a, from 7.8g (77 mmoles) of diisopropylamine, 48.2 ml of a 1.6M solution of n-butyllithium in hexane, 6.7 g (70 mmoles) of commercial cyclopentanecarbonitrile, 18 ml of 1,3-dimethylimidazolidin-2-one and 20.5 g (71.4 mmoles) of the compound prepared in example 93c, in 110 ml of dry tetrahydrofuran. After distillation, there is obtained 9.6 g (yield=60.0%) of a viscous liquid. b.p.0.4 =160° C.

Workup

  1. customObtained
  2. distillationAfter distillation

Sources & evidence

ORD record
ord-614f0f31742e48f785e71ddfb02e8507
Source dataset
uspto-grants-1995_02
Patent number
US05387709

Reaction notes

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