Sodium Hydroxide → 1-(4-Ethynylbenzyl)pyrrolidine

HRID 735005Notes

Reaction equation

HRID 735005 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:18]=[CH:17][C:10]([CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:9][CH:8]=1)(C)C.[OH-].[Na+]>ClCCl.CO>[C:6]([C:7]1[CH:18]=[CH:17][C:10]([CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:9][CH:8]=1)#[CH:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 688167401-(4-Trimethylsilanylethynylbenzyl)pyrrolidine

Product 1

HCID 860607941-(4-Ethynylbenzyl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.75 g (2.91 mmol) of 1-(4-trimethylsilanylethynylbenzyl)pyrrolidine in 10 mL of dichloromethane and 10 mL of methanol is combined with 2.4 mL of a 1M sodium hydroxide solution and stirred for 3 hours at ambient temperature. The reaction mixture is evaporated down and the residue is extracted with water and ethyl acetate. The organic phase is stirred with activated charcoal, filtered, and then dried over sodium sulfate. Yield: 0.4 g (74.1% of theory); C13H15N (M=185.27); calc.: molecular ion peak (M+H)+: 186; found: molecular ion peak (M+H)+: 186.

Workup

  1. customThe reaction mixture is evaporated down
  2. extractionthe residue is extracted with water and ethyl acetate
  3. stirringThe organic phase is stirred with activated charcoal
  4. filtrationfiltered
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-b2a57090acf04314b39821dd3ebcb8ff
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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