Hydrochloric Acid → HCID 57771421, compound

HRID 2070568Notes

Reaction equation

HRID 2070568 reaction equation
O[C:2]1([C:12]#[N:13])[CH2:11][CH2:10][C:5]2([CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:4][CH2:3]1.N1C=CC=CC=1.S(Cl)(Cl)=O.Cl>O1CCCC1>[CH2:9]1[C:5]2([CH2:10][CH2:11][C:2]([C:12]#[N:13])=[CH:3][CH2:4]2)[CH2:6][CH2:7][CH2:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 57771366HCID 57771366, compound

Product 1

HCID 57771421HCID 57771421, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-hydroxy-spiro[4.5]decane-8-carbonitrile (3.9 g) obtained in Step 1 in tetrahydrofuran (30 mL) were added successively pyridine (4.4 mL) and thionyl chloride (1.8 mL), followed by stirring the reaction mixture at room temperature for 15 hours. Then, after addition of 1N aqueous hydrochloric acid solution, the reaction mixture was extracted with diethyl ether. The organic layer was washed successively with 1N aqueous hydrochloric acid solution and saturated brine, dried and concentrated to give spiro[4.5]dec-7-ene-8-carbonitrile (2.8 g).

Workup

  1. extractionthe reaction mixture was extracted with diethyl ether
  2. washThe organic layer was washed successively with 1N aqueous hydrochloric acid solution and saturated brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-66a691e4f1094f7a891491e3fd3f4524
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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