Pyridine → 1-(Mesyloxymethyl)cyclohexanecarboxaldehyde

HRID 496167

Reaction equation

HRID 496167 reaction equation
[OH:1][CH2:2][C:3]1([CH:9]=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH3:11][S:12](Cl)(=[O:14])=[O:13].N1C=CC=CC=1>C(Cl)Cl>[S:12]([O:10][CH2:9][C:3]1([CH:2]=[O:1])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)([CH3:11])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 131063971-(Hydroxymethyl)-cyclohexanecarboxaldehyde

Product 1

HCID 223252611-(Mesyloxymethyl)cyclohexanecarboxaldehydeYield 77.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cold (0° C. mixture of alcohol 54 (75 g, 0.54 mole) and 65.29 g (0.57 mole) of methanesulfonyl chloride in 80 ml of methylene chloride was added a solution of pyridine (47.96 g, 0.57 mole) in 40 ml of methylene chloride. The reaction mixture was stirred at room temperature for 18 h then quenched with water, acidified with conc. HCl and extracted with methylene chloride. The organic layer was washed with water, brine, and dried over sodium sulfate and concentrated under vacuum to give 91.63 g (77.8%) of thick oil. Proton NMR and mass spectra were consistent with the product.

Workup

  1. customthen quenched with water
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-45dafcdbb98245a18e5c1716b6289a95
Source dataset
uspto-grants-2005_09
Patent number
US06943189B2

Linked notes

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