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

HRID 980906Notes

Reaction equation

HRID 980906 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

To 5 g of 4-hydroxy-4-(4-pyridyl)cyclohexanone ethyleneacetal dissolved in 40 ml of pyridine, there was added 8 ml of thionyl chloride at -10° C. After stirring the mixture at 0° C., the reaction mixture was poured into ice water. Then, an excess amount of aqueous sodium hydroxide solution was added. The reaction mixture was extracted with methylene chloride and purified. Thus, there was obtained 4 g of 4-(4-pyridyl)cyclohex-3-enone ethyleneacetal.

Workup

  1. extractionThe reaction mixture was extracted with methylene chloride
  2. custompurified

Sources & evidence

ORD record
ord-6135d322c9364c05a30f77440b5214e6
Source dataset
uspto-grants-1987_01
Patent number
US04639521

Reaction notes

Loading…