Tetramethylammonium hydroxide → HCID 70505759, compound

HRID 1680033Notes

Reaction equation

HRID 1680033 reaction equation
[CH3:1]/[C:2](=[CH:6]\[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[CH:9][CH:8]=1)/[C:3]([OH:5])=[O:4].[OH-].C[N+](C)(C)C>CO>[CH2:1]([O:4][C:3](=[O:5])/[C:2](/[CH3:1])=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:13][CH2:14][CH3:19]

Participants

4

Reactant 2

HCID 60966Tetramethylammonium hydroxideHCID 6437388(2E)-2-Methyl-3-[4-(3-pyridinylmethyl)phenyl]acrylic acid

Product 1

HCID 70505759HCID 70505759, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 126.5 mg of the acrylic acid(prepared as described in Example 15) in 3 ml of methanol was stirred with 0.1 ml of a 10% W/W solution of tetramethylammonium hydroxide in methanol at room temperature for 20 minutes, and the mixture was concentrated under reduced pressure. The residue was dissolved in 3 ml of N,N-dimethylformamide, the solution was stirred overnight with 0.1033 ml of decyl bromide at room temperature, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a 1% V/V solution of ethanol in chloroform as eluent to give 53 mg of the title compound having the following physical characteristics:

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 3 ml of N,N-dimethylformamide
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel using a 1% V/V solution of ethanol in chloroform as eluent

Sources & evidence

ORD record
ord-548119cbbe4240299c35dbefdc3c860e
Source dataset
uspto-grants-1981_06
Patent number
US04271170

Reaction notes

Loading…