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Water → {2-[4-(Trifluoromethyl)phenyl]-1,3-oxazol-4-yl}methyl methylsulfonate

HRID 585070
Notes
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Reaction equation

HRID 585070 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH:11]=[C:12]([CH2:14][OH:15])[N:13]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27].O>O1CCCC1>[CH3:25][S:26]([O:15][CH2:14][C:12]1[N:13]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:16])[F:17])=[CH:8][CH:7]=2)[O:10][CH:11]=1)(=[O:28])=[O:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22064105{2-[4-(Trifluoromethyl)phenyl]-1,3-oxazol-4-yl}methanol

Product 1

HCID 22064284{2-[4-(Trifluoromethyl)phenyl]-1,3-oxazol-4-yl}methyl methylsulfonate

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
0 °C

Procedure

A solution of {2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl}methan-1-ol (0.19 g, 0.78 mmol) in tetrahydrofuran (15 ml) was cooled to 0° C., and triethylamine (0.33 ml, 2,34 mmol) was added, followed by methanesulfonyl chloride (0.12 ml, 1.56 mmol) dropwise. The mixture was stirred for 1 hour at 0° C., then water was added, and product was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and solvent removed from the filtrate under reduced pressure, to yield {2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl}methyl methylsulfonate, the mesyl derivative of a compound of formula (15),

Workup

  1. extractionproduct was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate, and solvent
  3. customremoved from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-04ca0f5b35e04a0f9e85ec7e3f581f18
Source dataset
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06930111B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes