Water → 5-Bromo-2-(1,4-dioxaspiro[4,5]decane-8-yl)pyridine

HRID 1748521Notes

Reaction equation

HRID 1748521 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2(C(O)=O)[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.O>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 962WaterHCID 86692469HCID 86692469, compound

Product 1

HCID 866924705-Bromo-2-(1,4-dioxaspiro[4,5]decane-8-yl)pyridineYield 95.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 8-(5-bromopyridin-2-yl)-1,4-dioxaspiro[4,5]decane-8-carboxylic acid (776 mg) in dimethylsulfoxide (3 ml) was stirred at 150° C. for 1.5 hours. After completion of the reaction, the reaction solution was left stand to room temperature, water was added and extracted with ethyl acetate. The organic solution was washed with water and saturated brine successively, dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 5-bromo-2-(1,4-dioxaspiro[4,5]decane-8-yl)pyridine (646 mg) as a colorless oil.

Workup

  1. customAfter completion of the reaction
  2. waitthe reaction solution was left stand to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic solution was washed with water and saturated brine successively
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5118ec4367134c6eb7f59ac36ad38b3a
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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