Trifluoromethanesulfonic anhydride → HCID 117728745, compound

HRID 718685Notes

Reaction equation

HRID 718685 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1.[O:18](S(C(F)(F)F)(=O)=O)[S:19]([C:22]([F:25])([F:24])[F:23])(=O)=[O:20]>C(Cl)Cl>[F:23][C:22]([F:25])([F:24])[S:19]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][O:10][CH2:11]2)=[CH:4][CH:3]=1)(=[O:20])=[O:18]

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 89782575HCID 89782575, compound

Product 1

HCID 117728745HCID 117728745, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 2-[3-(4-hydroxyphenyl)oxetan-3-yl]acetate (500 mg, 2.12 mmol), TEA (321 mg, 3.17 mmol), and DCM (40 mL) was added dropwise a solution of Tf2O (658 mg, 2.33 mmol) in DCM (20 mL) in 15 min at −5° C. (ice/salt bath). After stirring for an hour, the reaction was quenched by the addition of water (50 mL). The crude mixture was extracted with DCM (2×40 mL). The organic layers were combined and concentrated to a residue which purified by flash column chromatography on silica gel (1-5% EtOAc/petroleum ether) to afford compound 67a as white oil. Mass Spectrum (LCMS, ESI pos.): Calcd. for C14H15F3O6S: 369.3 (M+H). found: 369.1.

Workup

  1. customthe reaction was quenched by the addition of water (50 mL)
  2. extractionThe crude mixture was extracted with DCM (2×40 mL)
  3. concentrationconcentrated to a residue which
  4. custompurified by flash column chromatography on silica gel (1-5% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-427c64ceba7d42fcae6eac77b3bff948
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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