Hydrochloric Acid → HCID 57983509, compound

HRID 1868911Notes

Reaction equation

HRID 1868911 reaction equation
[CH3:1][C:2]([C:6]1[C:11]([C:12]#[C:13][Si](C)(C)C)=[CH:10][CH:9]=[CH:8][N:7]=1)([CH3:5])[C:3]#[N:4].C1COCC1.[OH-].[Na+].Cl>CCOC(C)=O.CCCCCC>[C:12]([C:11]1[C:6]([C:2]([CH3:5])([CH3:1])[C:3]#[N:4])=[N:7][CH:8]=[CH:9][CH:10]=1)#[CH:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57983432HCID 57983432, compound

Product 1

HCID 57983509HCID 57983509, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of 2-methyl-2-(3-(2-(trimethylsilyl)ethynyl)pyridin-2-yl)propanenitrile (1.6 g, 6.6 mmol) and THF (20 mL, 244 mmol), was added NaOH (13 mL, 66 mmol). After 1.5 hours, TLC (30% EtOAc/hexane) showed complete reaction to provide a product with a lower spot. The reaction was acidified with 5N HCl (pH=2) and then was extracted with EtOAc. The organic layer was washed with water and brine (3× each) and then dried over MgSO4 and concentrated in vacuo to give a yellow oil. The crude product was purified by silica flash chromatography (0-75% EtOAc/hexane) to give the desired product as a light-orange crystalline solid (0.93 g, 83%). MS (m/z)=171 (M+H)+. Calculated for C11H10N2 170.2.

Workup

  1. customreaction
  2. customto provide a product with a lower spot
  3. extractionwas extracted with EtOAc
  4. washThe organic layer was washed with water and brine (3× each) and
  5. dry with materialthen dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give a yellow oil
  8. customThe crude product was purified by silica flash chromatography (0-75% EtOAc/hexane)

Sources & evidence

ORD record
ord-e9072184adfe4c27877de1af07406b20
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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