Diisopropylamine → HCID 66747345, compound

HRID 331706Notes

Reaction equation

HRID 331706 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]#[N:23])[CH:18]=[CH:19][CH:20]=1.Br[CH2:32][C:33]([O:35][CH3:36])=[O:34]>O1CCCC1.Cl>[CH3:36][O:35][C:33](=[O:34])[CH2:32][C:21]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:22]#[N:23])[C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH3:13])[CH:16]=1

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 60984Methyl bromoacetateHCID 66746775HCID 66746775, compoundHCID 178418339Butyllithium

Product 1

HCID 66747345HCID 66747345, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of diisopropylamine (0.7 ml, 5.1 mmol) in 20 ml dry tetrahydrofuran at −78° C. was added n-butyl lithium (1.6 M in hexan, 3.2 ml, 5.1 mmol) and stirred for 1 h. A solution of 2-(3-methoxy-phenyl)-3-phenyl-propionitrile (1.0 g, 4.2 mmol) in 5 ml dry tetrahydrofuran was added to the mixture, stirred for 30 min, followed by addition of methyl 2-bromoacetate (0.6 ml, 6.3 mmol). The mixture was stirred over night at room temperature, diluted with 50 ml 1M HCl and the resulting mixture extracted with dichloromethane. The organic layer was washed with water and brine, dried over sodium bicarbonate, filtered and the solvent evaporated to obtain a yellow oil (1.3 g). Purification on 12 g SiO2 using dichloromethane afforded a clear colourless oil.

Workup

  1. stirringstirred for 30 min
  2. stirringThe mixture was stirred over night at room temperature
  3. extractionthe resulting mixture extracted with dichloromethane
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium bicarbonate
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-ad1a20074bad42faa40f719305b7dd5f
Source dataset
uspto-grants-2014_11
Patent number
US08877794B2

Reaction notes

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