Pyridine → 5-Bromo-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-3-methylpyridine

HRID 1748526Notes

Reaction equation

HRID 1748526 reaction equation
N1C=CC=CC=1.[Br:7][C:8]1[CH:9]=[C:10]([CH3:25])[C:11]([C:14]2(O)[CH2:23][CH2:22][C:17]3([O:21][CH2:20][CH2:19][O:18]3)[CH2:16][CH2:15]2)=[N:12][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.S(Cl)(Cl)=O>[Br:7][C:8]1[CH:9]=[C:10]([CH3:25])[C:11]([C:14]2[CH2:23][CH2:22][C:17]3([O:21][CH2:20][CH2:19][O:18]3)[CH2:16][CH:15]=2)=[N:12][CH:13]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 10340Sodium CarbonateHCID 866924748-(5-Bromo-3-methylpyridin-2-yl)-1,4-dioxaspiro[4,5]decan-8-ol

Product 1

HCID 866924755-Bromo-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-3-methylpyridineYield 49.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

Pyridine (42.7 ml) was added to a solution of 8-(5-bromo-3-methylpyridin-2-yl)-1,4-dioxaspiro[4,5]decan-8-ol (28 g) in dichloromethane (300 ml), thionyl chloride (19 ml) was added dropwise under ice cooling and the reaction solution was warmed to room temperature and stirred for an hour. After completion of the reaction, the reaction solution was poured into 10% aqueous solution of sodium carbonate, stirred and the resulting precipitate was collected by filtration and dried at 60° C. under air blow to give the titled compound (13.1 g) as a pale yellow solid.

Workup

  1. additionwas added dropwise under ice cooling
  2. customAfter completion of the reaction
  3. stirringstirred
  4. filtrationthe resulting precipitate was collected by filtration
  5. customdried at 60° C. under air blow

Sources & evidence

ORD record
ord-ff907f620b5844b0afe9b494c75fce33
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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