Trifluoroacetic acid → HCID 86691559, compound

HRID 514113Notes

Reaction equation

HRID 514113 reaction equation
C([O:5][CH:6]([C:12]1[C:21]([CH3:22])=[C:20]([F:23])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[O:24][S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.O>[F:23][C:20]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([O:24][S:25]([C:28]([F:30])([F:29])[F:31])(=[O:26])=[O:27])=[C:12]([CH:6]([OH:5])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:21]=1[CH3:22]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86691560HCID 86691560, compound

Product 1

HCID 86691559HCID 86691559, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 2-tert-butoxy-2-(4-fluoro-3-methyl-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate (1.75 g, 3.76 mmol) in DCM (30 mL) was treated dropwise with TFA (3.0 mL) over 3 min at 23° C. After 16 h, the reaction was diluted with H2O (60 mL) and the system was extracted with DCM (3×20 mL). Combined organic layers were dried (Na2SO4), filtered, and concentrated giving the crude desired product (˜1.54 g obtained), which was used in the next reaction. 1H NMR (400 MHz, CDCl3) δ 8.11-8.06 (m, 1H), 7.67-7.64 (m, 1H), 7.61-7.52 (m, 2H), 7.41 (d, J=7.8 Hz, 1H), 5.79 (s, 1H), 4.34-4.22 (m, 2H), 2.40 (d, JHF=3.2 Hz, 3H), 1.22 (t, J=7.4 Hz, 3H). 19F NMR (377 MHz, CDCl3) δ−122.6 (app. s, 1F), −73.3 (s, 3F).

Workup

  1. extractionthe system was extracted with DCM (3×20 mL)
  2. dry with materialCombined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b21163a2532b4447a32fe4d5206ff57e
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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