Sodium Hydroxide → 4-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)pyridine

HRID 231216Notes

Reaction equation

HRID 231216 reaction equation
[CH2:1]1[O:17][C:4]2([CH2:9][CH2:8][C:7](O)([C:10]3[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=3)[CH2:6][CH2:5]2)[O:3][CH2:2]1.S(Cl)(Cl)=O.[OH-].[Na+]>N1C=CC=CC=1>[CH2:2]1[O:3][C:4]2([CH2:9][CH2:8][C:7]([C:10]3[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=3)=[CH:6][CH2:5]2)[O:17][CH2:1]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 137720538-(4-Pyridinyl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 137720544-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)pyridineYield 86.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

In 40 ml of pyridine was dissolved 5 g of 4-hydroxy-4-(4-pyridyl)cyclohexanone ethyleneacetal and, 8 ml of thionyl chloride was added to the solution at -10° C. Then, after stirring at 0° C., the reaction solution was poured onto ice. After an excess of a sodium hydroxide aqueous solution was added to the mixture, it was extracted with methylene chloride and the extract was purified to give 4 g of 4-(4-pyridyl)cyclohex-3-enone ethyleneacetal.

Workup

  1. additionwas added to the solution at -10° C
  2. additionthe reaction solution was poured onto ice
  3. extractionwas extracted with methylene chloride
  4. customthe extract was purified

Sources & evidence

ORD record
ord-12eda7caa35749199f0b61e7c09707eb
Source dataset
uspto-grants-1989_07
Patent number
US04845228

Reaction notes

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