Thionyl Chloride → 2-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)pyridine

HRID 1173180Notes

Reaction equation

HRID 1173180 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1(O)[CH2:16][CH2:15][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:9][CH2:8]1.O=S(Cl)Cl>N1C=CC=CC=1>[O:14]1[C:10]2([CH2:15][CH2:16][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:8][CH2:9]2)[O:11][CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21187637HCID 21187637, compound

Product 1

HCID 211876502-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)pyridineYield 83.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The ketal (2 g, 8.5 mmol) obtained from step A, Example 7 was dissolved in pyridine (40 mL) and the solution was cooled in an ice bath. To it was added SOCl2 (3.1 mL, 42.5 mmol). The solution was allowed to warm to room temperature and stirring was continued overnight. The reaction was quenched by addition of ice and then water. The resulting solution was extracted with EtOAc three times. The combined EtOAc layer was dried over MgSO4 and concentrated. Flash chromatography on silica gel eluting with 0 to 55% EtOAc/hexanes provided 1.54 g of the title compound. MS calculated (M+H)+ 218, found 218.

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. customThe reaction was quenched by addition of ice
  3. extractionThe resulting solution was extracted with EtOAc three times
  4. dry with materialThe combined EtOAc layer was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6d5106fe54914368b1289b0161d41259
Source dataset
uspto-grants-2010_11
Patent number
US07834021B2

Reaction notes

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