Pyridine → HCID 19860691, compound

HRID 2413849Notes

Reaction equation

HRID 2413849 reaction equation
[F:1][C:2]([F:8])([CH2:5][CH2:6][OH:7])[CH2:3][OH:4].N1C=CC=CC=1.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>ClCCl>[CH3:15][S:16]([O:4][CH2:3][C:2]([F:8])([F:1])[CH2:5][CH2:6][O:7][S:16]([CH3:15])(=[O:18])=[O:17])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 13935577108781-20-0

Product 1

HCID 19860691HCID 19860691, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 2,2-difluoro-1,4-butanediol (12.97 g, 103 mM), dry pyridine (65 mL) and dichloromethane (200 mL), is slowly added a solution of methanesulfonyl chloride (23.6 g) in dichloromethane (50 mL). Stirring is continued overnight, and the mixture is washed with 2N HCl (twice), 10% aqueous NaHCO3 until neutral, and finally with water. The organic solution is dried (MgSO4) and evaporated to yield 1,4-bis-methanesulfonyloxy-2,2-difluorobutane as a slightly yellow oil (25.4 g, 87.5%) which crystallizes on scratching with dry ether: white crystals, 22.3 g (77%).

Workup

  1. washthe mixture is washed with 2N HCl (twice), 10% aqueous NaHCO3 until neutral, and finally with water
  2. dry with materialThe organic solution is dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-f48a691379d84dec80926be71d5f74f5
Source dataset
uspto-grants-1988_01
Patent number
US04719313

Reaction notes

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