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

HRID 2041580Notes

Reaction equation

HRID 2041580 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:14])[CH2:10][CH:11]([CH3:13])[CH3:12])=[N:7][CH:8]=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:4]=[CH:5][C:6]([C:9](=[O:14])[CH2:10][CH:11]([CH3:12])[CH3:13])=[N:7][CH:8]=1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 576561925-Hydroxymethyl-2-(3-methyl-butyryl)-pyridine

Product 1

HCID 576563455-Methanesulfonyloxymethyl-2-(3-methyl-butyryl)-pyridineYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolve 5-hydroxymethyl-2-(3-methyl-butyryl)-pyridine (210 mg, 1.086 mmol) in dichloromethane (5 mL). Cool to 0° C. and add triethylamine (0.167 mL, 1.195 mmol) and methanesulfonyl chloride (0.093 mL, 1.195 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 (256 mg, 87%). GC-MS m/z: 271

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-cf4d8b0aa1d94ecf80b5f64b8fc2c2b7
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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