Acetic Acid → 2-[2-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethynyl]-5-acetoxymethylpyridine

HRID 1886084Notes

Reaction equation

HRID 1886084 reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][OH:23])=[CH:18][N:17]=3)[CH:5]=[CH:4][C:3]1=2.[C:25](O)(=[O:27])[CH3:26].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][O:23][C:25](=[O:27])[CH3:26])=[CH:18][N:17]=3)[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 10868DicyclohexylcarbodiimideHCID 193728362-[2-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethynyl]-5-hydroxymethylpyridine

Product 1

HCID 193728152-[2-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethynyl]-5-acetoxymethylpyridine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3.195 g (10 mmol) of 2-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethynyl]-5-hydroxymethylpyridine, 600 mg (10 mmol) of glacial acetic acid, 2.06 g (10 mmol) of dicyclohexylcarbodiimide and 460 mg (3.765 mmol) of 4-dimethylaminopyridine in 150 ml methylene chloride is stirred at room temperature for 48 hours. The reaction mixture is then filtered and the residue washed with 50 ml of methylene chloride. The filtrate is then concentrated in vacuo and the residue is purified by chromatography followed by recrystallation to give the title compound.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. washthe residue washed with 50 ml of methylene chloride
  3. concentrationThe filtrate is then concentrated in vacuo
  4. customthe residue is purified by chromatography

Sources & evidence

ORD record
ord-667bed0accbd46c99aac60a48c08bee6
Source dataset
uspto-grants-1992_09
Patent number
US05149705

Reaction notes

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