Pyridine → HCID 21409554, compound

HRID 1414147Notes

Reaction equation

HRID 1414147 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][S:6]([O:9][C:10]1[CH:11]=[CH:12][C:13]2[O:17][CH:16](O)[C:15]([CH3:20])([CH3:19])[C:14]=2[CH:21]=1)(=[O:8])=[O:7].N1C=CC=CC=1>C(Cl)Cl>[CH3:5][S:6]([O:9][C:10]1[CH:11]=[CH:12][C:13]2[O:17][CH:16]([Cl:3])[C:15]([CH3:20])([CH3:19])[C:14]=2[CH:21]=1)(=[O:8])=[O:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 536079(2-Hydroxy-3,3-dimethyl-2H-1-benzofuran-5-yl) methanesulfonate

Product 1

HCID 21409554HCID 21409554, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of thionyl chloride (72 parts) in methylene chloride (270 parts) was added dropwise over a period of 30 minutes to a mixture of 2,3-dihydro-2-hydroxy-3,3-dimethyl-5-benzofuranyl methanesulphonate (130 parts) and pyridine (48 parts) in methylene chloride (1,300 parts) cooled in an ice bath. After stirring for three hours, the solution was washed twice with water, dried over sodium sulphate and the solvent distilled off under reduced pressure. The brown liquid which remained solidified to form 2-chloro-2,3-dihydro-3,3-dimethyl-5-benzofuranyl methanesulphonate (135 parts, 97% yield), melting point 59°-61° C, confirmed by its elemental analysis:

Workup

  1. temperaturecooled in an ice bath
  2. washthe solution was washed twice with water
  3. dry with materialdried over sodium sulphate
  4. distillationthe solvent distilled off under reduced pressure

Sources & evidence

ORD record
ord-1d0aec94337e45ef836564cb3f822755
Source dataset
uspto-grants-1977_01
Patent number
US04001003

Reaction notes

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