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

HRID 621706Notes

Reaction equation

HRID 621706 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

5 g of 4-hydroxy-4-(4-pyridyl)cyclohexanone ethylene acetal was dissolved in 40 ml of pyridine and 8 ml of thionyl chloride was added thereto at -10° C. The obtained mixture was stirred at 0° C. and poured onto ice and an excessive amount of an aqueous solution of sodium hydroxide was added thereto. After purifying the reaction mixture by extracting with methylene chloride, 4 g of 4-(4-pyridyl)cyclohex-3-enone ethylene acetal was obtained. m.p.: 67°-70° C. NMRδTMSCDCl3 : 1.86 (2H, t), 2.4-2.7 (4H, m), 4.04 (4H, s), 6.24 (1H, t), 7.28 (2H, d) and 8.52 (2H, d).

Workup

  1. customat -10° C
  2. additionpoured onto ice
  3. customAfter purifying the reaction mixture
  4. extractionby extracting with methylene chloride

Sources & evidence

ORD record
ord-dcfeb61e0fb546559248f254622febe5
Source dataset
uspto-grants-1989_04
Patent number
US04824952

Reaction notes

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