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

HRID 2041577Notes

Reaction equation

HRID 2041577 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-77704a653be445cca9057efc36232bac
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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