Trimethylsilyl cyanide → 2-Hydroxy-3-methoxy-3-(4-morpholinophenyl)propanenitrile

HRID 56580Notes

Reaction equation

HRID 56580 reaction equation
[CH3:1][O:2][CH:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1)[CH:4]=[O:5].C[Si]([C:22]#[N:23])(C)C.C([O-])(O)=O.[Na+]>CCOCC.CCOC(C)=O.O.[Zn+2].[I-].[I-]>[OH:5][CH:4]([CH:3]([O:2][CH3:1])[C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:10][CH:11]=1)[C:22]#[N:23]

Participants

8

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 516892Sodium BicarbonateHCID 58432110HCID 58432110, compound

Product 1

HCID 584320842-Hydroxy-3-methoxy-3-(4-morpholinophenyl)propanenitrileYield 94.2%

Reagents, catalysts & solvents 4

HCID 9883512zinc(II)iodideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-methoxy-2-(4-morpholinophenyl)acetaldehyde (1.27 g, ˜5.1 mmol) in Et2O (35 mL) under a drying tube was added trimethylsilyl cyanide (1 mL, 8 mmol) and ZnI2 (50 mg, 0.16 mmol). After stirring at room temperature for 15.5 hrs, saturated aqueous NaHCO3 was added and the mixture was stirred several hrs. The mixture was diluted with EtOAc and H2O and the layers were separated. The organic layers were washed with saturated aqueous NaHCO3, dried over Na2SO4 and concentrated in vacuo to give 2-hydroxy-3-methoxy-3-(4-morpholinophenyl)propanenitrile as an orange foam (1.26 g). The product was used without further purification.

Workup

  1. stirringthe mixture was stirred several hrs
  2. customthe layers were separated
  3. washThe organic layers were washed with saturated aqueous NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f800aa439e843318ebf9270985e5f71
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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