Pyridine → HCID 54197444, compound

HRID 1384864Notes

Reaction equation

HRID 1384864 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][C:7](=[O:9])[CH2:6][CH2:5][O:4]1.N1C=CC=CC=1.[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1)([O-:18])=[O:17]>C(Cl)(Cl)Cl>[O:9]=[C:7]1[CH2:6][CH2:5][O:4][CH:3]([CH2:2][O:1][S:25]([C:22]2[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[CH:24][CH:23]=2)(=[O:26])=[O:27])[CH2:8]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 74044-Nitrobenzenesulfonyl chlorideHCID 21936766243968-13-0

Product 1

HCID 54197444HCID 54197444, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 2-hydroxymethyl-tetrahydro-pyran-4-one (625 mg, 4.81 mmol) in a mixture of pyridine (778 μl, 9.62 mmol) and chloroform (6.0 ml) at 0° C. under nitrogen was slowly added 4-nitrobenzenesulfonyl chloride (1.60 g, 7.22 mmol). The mixture was allowed to warm to room temperature and stirred for 3 h. Chloroform (30 ml) was added and the solution washed with 2.0 N hydrochloric acid (3×10 ml), 5% NaHCO3 (3×10 ml) and water (3×10 ml). The organic phase was dried (Na2SO4), filtered and the solvent evaporated in vacuo. The solid residue was purified by column chromatography on silica gel using a gradient of dichloromethane:hexane:ethyl acetate (1:1:0 to 8:0:2) as eluent. Pure fractions were collected and the volatiles were evaporated in vacuo affording 0.98 g (65%) of 4-nitro-benzenesulfonic acid 4-oxo-tetrahydro-pyran-2-ylmethyl ester as a solid.

Workup

  1. washthe solution washed with 2.0 N hydrochloric acid (3×10 ml), 5% NaHCO3 (3×10 ml) and water (3×10 ml)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo
  5. customThe solid residue was purified by column chromatography on silica gel using a gradient of dichloromethane:hexane:ethyl acetate (1:1:0 to 8:0:2) as eluent
  6. customPure fractions were collected
  7. customthe volatiles were evaporated in vacuo

Sources & evidence

ORD record
ord-cf2b6bae850843eb9226fb2f28c2e040
Source dataset
uspto-grants-2001_07
Patent number
US06262044B1

Reaction notes

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