Tetrahydrofuran → 3-Chloro-5-ethenyloxypyridine

HRID 1266969Notes

Reaction equation

HRID 1266969 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([O:12][CH2:13][CH2:14]O)[CH:11]=1.O1CCCC1.[OH-].[K+]>C(O)(C)(C)C>[Cl:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([O:12][CH:13]=[CH2:14])[CH:11]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 24386Thionyl ChlorideHCID 115573693-Chloro-5-(2-hydroxyethoxy)pyridine

Product 1

HCID 108208043-Chloro-5-ethenyloxypyridine

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
50 °C

Procedure

Thionyl chloride (58.6 g, 493 mmol) was added to a mixture of 3-chloro5-(2-hydroxyethoxy)pyridine (14.5 g, 82.1 mmol) and tetrahydrofuran (100 ml). The mixture was stirred for 1 h at 50° C. The mixture was evaporated. Potassium hydroxide (9.0 g, 164 mmol) and tert-butanol (100 ml) were added and the mixture was stirred for 3 days at 100° C. The solvent was evaporated. Water (150 ml) was added and the mixture was extracted twice with diethyl ether (100 ml). Yield 6.77 g, 53%.

Workup

  1. customThe mixture was evaporated
  2. stirringthe mixture was stirred for 3 days at 100° C
  3. customThe solvent was evaporated
  4. additionWater (150 ml) was added
  5. extractionthe mixture was extracted twice with diethyl ether (100 ml)

Sources & evidence

ORD record
ord-9b0583dacccc4b5dba27fe46ff369f61
Source dataset
uspto-grants-2003_04
Patent number
US06552012B2

Reaction notes

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