1,3-Dimethyl-2-imidazolidinone → 4-[[4-(2-Hydroxyethyl)phenyl]methyl]tetrahydropyran-4-carbonitrile

HRID 274124Notes

Reaction equation

HRID 274124 reaction equation
C(N[CH:5]([CH3:7])[CH3:6])(C)C.C([Li])CCC.C[N:14]1[CH2:18][CH2:17]N(C)C1=O.[O:21]1[CH2:26][CH2:25][CH:24]([C:27]#N)[CH2:23][CH2:22]1.[O:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>CCCCCC>[OH:21][CH2:26][CH2:25][C:24]1[CH:27]=[CH:7][C:5]([CH2:6][C:17]2([C:18]#[N:14])[CH2:32][CH2:33][O:29][CH2:30][CH2:31]2)=[CH:22][CH:23]=1

Participants

7

Reactant 5

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 7912DiisopropylamineHCID 8028Tetrahydrofuran2×HCID 11815837Oxane-4-carbonitrileHCID 178418339Butyllithium

Product 1

HCID 189995784-[[4-(2-Hydroxyethyl)phenyl]methyl]tetrahydropyran-4-carbonitrileYield 75.5%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Obtained by operating as in example 87a, from 6.3 g (62.2 mmoles) of diisopropylamine in 104 ml of tetrahydrofuran, 38.7 ml (62.0 mmoles) of a 1.6M solution of n-butyllithium in hexane, 9.3 g of 1,3-dimethylimidazolidin-2-one, 8.8 g (56.7 mmoles) of 2,3,5,6-tetrahydro-4H-pyran-4-carbonitrile (prepared according to Gibson C. S. and Johnson J. D. A., J. Chem. Soc. (1930), 2525-30) in 93 ml tetrahydrofuran and 17.7 g (62 mmoles) of the compound prepared in example 26a. After purification by chromatography on a column of silica in a hexane-ethyl acetate (1:1) mixture, there is obtained 10.5 g (yield=75.5%) oil.

Workup

  1. customObtained
  2. customprepared
  3. customAfter purification by chromatography on a column of silica in a hexane-ethyl acetate (1:1) mixture

Sources & evidence

ORD record
ord-b6e59e49d55d41bdaf43583b7aaccc68
Source dataset
uspto-grants-1995_02
Patent number
US05387709

Reaction notes

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