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

HRID 1193340Notes

Reaction equation

HRID 1193340 reaction equation
O=S(Cl)Cl.[N:5]1[CH:10]=[CH:9][C:8]([C:11]2(O)[CH2:20][CH2:19][C:14]3([O:18][CH2:17][CH2:16][O:15]3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[O:18]1[C:14]2([CH2:19][CH2:20][C:11]([C:8]3[CH:7]=[CH:6][N:5]=[CH:10][CH:9]=3)=[CH:12][CH2:13]2)[O:15][CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 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 63%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

SOCl2(10.5 ml) was added dropwise at −10° C. to a solution of 8-(pyridin-4-yl)-1,4-dioxa-spiro[4.5]decan-8-ol (6.0 g, 25.5 mmol, 1 eq) in pyridine (50 ml), and stirring was carried out for 15 min. After monitoring by thin-layer chromatography, the reaction mixture was poured carefully onto ice (100 g), neutralized with sat. sodium hydrogen carbonate solution (100 ml) and extracted with dichloromethane (2×150 ml). The combined organic phases were washed with water (100 ml) and sat. NaCl solution (100 ml), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 1% MeOH in dichloromethane). Yield: 63% (3.5 g, 16.1 mmol).

Workup

  1. additionthe reaction mixture was poured carefully onto ice (100 g)
  2. extractionextracted with dichloromethane (2×150 ml)
  3. washThe combined organic phases were washed with water (100 ml) and sat. NaCl solution (100 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography (silica gel, 1% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-ad636760abaf492b948d0a9765af3b44
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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