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Triethylamine → 2-[4-(5-Methyl-2-phenyl-4-oxazolylmethoxy)phenyl]ethyl methanesulfonate

HRID 349905
Notes
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Reaction equation

HRID 349905 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][C:7]1[O:11][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:9][C:8]=1[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][OH:28])=[CH:22][CH:21]=1.C(N(CC)CC)C.C(OCC)(=O)C>O>[CH3:1][S:2]([O:28][CH2:27][CH2:26][C:23]1[CH:22]=[CH:21][C:20]([O:19][CH2:18][C:8]2[N:9]=[C:10]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[O:11][C:7]=2[CH3:6])=[CH:25][CH:24]=1)(=[O:4])=[O:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 691720772-[4-(5-Methyl-2-phenyl-4-oxazolylmethoxy)phenyl]ethan-1-ol

Product 1

HCID 867604162-[4-(5-Methyl-2-phenyl-4-oxazolylmethoxy)phenyl]ethyl methanesulfonateYield 96.3%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

Methanesulfonyl chloride (3.37 g) was added dropwise to a mixture of 2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]ethan-1-ol (7.0 g), triethylamine (2.97 g), and ethyl acetate (300 ml) at 0° C., and the mixture was stirred for 3 hours at room temperature. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium bicarbonate, 1N hydrochloric acid and then with saturated aqueous sodium chloride solution, then dried (MgSO4), and concentrated. The crystals obtained were collected by filtration to yield 2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]ethyl methanesulfonate (8.44 g, yield: 96%). This was recrystallized from ethyl acetate-hexane. Melting point: 66–67° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium bicarbonate, 1N hydrochloric acid
  3. dry with materialwith saturated aqueous sodium chloride solution, then dried (MgSO4)
  4. concentrationconcentrated
  5. customThe crystals obtained
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-c3290d0df06b457797acaa0291625be1
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07179823B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes