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Triethylamine → [5-(2,2,2-Trifluoroethoxy)pyridin-2-yl]methyl methanesulfonate

HRID 1477602
Notes
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Reaction equation

HRID 1477602 reaction equation
[F:1][C:2]([F:14])([F:13])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][OH:12])=[N:9][CH:10]=1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[CH3:22][S:23]([O:12][CH2:11][C:8]1[CH:7]=[CH:6][C:5]([O:4][CH2:3][C:2]([F:1])([F:13])[F:14])=[CH:10][N:9]=1)(=[O:25])=[O:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66893281(5-(2,2,2-Trifluoroethoxy)pyridin-2-yl)methanol

Product 1

HCID 117839939[5-(2,2,2-Trifluoroethoxy)pyridin-2-yl]methyl methanesulfonateYield 67.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution (2.8 mL) of [5-(2,2,2-trifluoroethoxy)pyridin-2-yl]methanol (138 mg, 0.67 mmol), triethylamine (468 μL, 3.33 mmol) and methanesulfonyl chloride (77.4 μL, 1.00 mmol) were added at 0° C. and the resultant solution was stirred for 30 minutes. After completion of the reaction, the reaction solution was washed with saturated ammonium chloride aqueous solution and brine. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a crude product (129 mg) of the title compound.

Workup

  1. customAfter completion of the reaction
  2. washthe reaction solution was washed with saturated ammonium chloride aqueous solution and brine
  3. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b8f01f2fa8b2467599ea3a2da4c36872
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09403798B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes