Hydrochloric Acid → HCID 86629257, compound

HRID 1868702Notes

Reaction equation

HRID 1868702 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]([CH3:14])[C:12]#[N:13].[OH-].[Na+].Cl>C1COCC1>[C:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]([CH3:14])[C:12]#[N:13])#[CH:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67099658HCID 67099658, compound

Product 1

HCID 86629257HCID 86629257, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2-(2-(Trimethylsilyl)ethynyl)phenyl)propanenitrile (2.16 g, 9 mmol) was stirred with 5N NaOH (10 mL, 50 mmol) and THF (20 mL) at room temperature for 1 hour. The reaction mixture was acidified with 5N HCl (13 mL) until the pH was about 2. The aqueous mixture was then extracted with EtOAc (3×50 mL). The combined organic layers were extracted with water (3×50 mL) and once with brine (50 mL), dried with MgSO4, and concentrated in vacuo to afford a brown oil. MS (m/z)=156 (M+H)+.

Workup

  1. extractionThe aqueous mixture was then extracted with EtOAc (3×50 mL)
  2. extractionThe combined organic layers were extracted with water (3×50 mL) and once with brine (50 mL)
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated in vacuo
  5. customto afford a brown oil

Sources & evidence

ORD record
ord-31508ad39c7f4c27ab9389d36b8b0950
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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