Triethylamine → 2-Methanesulfonyloxymethyl-5-(3-methyl-butyryl)-pyridine

HRID 911714Notes

Reaction equation

HRID 911714 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:14])[CH2:10][CH:11]([CH3:13])[CH3:12])=[CH:5][N:4]=1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[CH3:22][S:23]([O:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:14])[CH2:10][CH:11]([CH3:12])[CH3:13])=[CH:5][N:4]=1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 576564172-Hydroxymethyl-5-(3-methyl-butyryl)-pyridine

Product 1

HCID 576565872-Methanesulfonyloxymethyl-5-(3-methyl-butyryl)-pyridineYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolve 2-hydroxymethyl-5-(3-methyl-butyryl)-pyridine (190 mg, 0.98 mmol) in dichloromethane (10 mL). Cool to 0° C. and add triethylamine (0.151 mL, 1.08 mmol) and methanesulfonyl chloride (0.083 mL, 1.08 mmol). Allow the mixture to warm to room temperature and stir for 2 h. Dilute the reaction mixture with dichloromethane and wash with saturated aqueous NaHCO3. Dry the organic phase over Na2SO4, filter and concentrate in vacuo to provide the title compound as oil (263 mg, 98%).

Workup

  1. temperatureAllow the mixture to warm to room temperature
  2. washwash with saturated aqueous NaHCO3
  3. dry with materialDry the organic phase over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-56f1bd56b1764cbb81f5aa48614e6ce7
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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