Trifluoroacetic acid → HCID 86691576, compound

HRID 926205Notes

Reaction equation

HRID 926205 reaction equation
C([O:5][CH:6]([C:12]1[C:21]([CH3:22])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[O:23][S:24]([C:27]([F:30])([F:29])[F:28])(=[O:26])=[O:25])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.O>[OH:5][CH:6]([C:12]1[C:21]([CH3:22])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[O:23][S:24]([C:27]([F:30])([F:28])[F:29])(=[O:25])=[O:26])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86691577HCID 86691577, compound

Product 1

HCID 86691576HCID 86691576, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 2-tert-butoxy-2-(3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate (6.0 grams, ˜13 mmol, semi pure) in DCM (60 mL) was treated with TFA (6.0 mL) at 23° C. The reaction was diluted with H2O (60 mL) and the organic phase collected. The aqueous layer was extracted with DCM (2×30 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue (5.5 grams) was used in the next reaction without further purification. 1H NMR (400 MHz, CDCl3): 8.08-8.06 (m, 1H), 7.81-7.78 (m, 1H), 7.69 (s, 1H), 7.62-7.55 (m, 2H), 5.81 (app. s, 1H), 4.35-4.21 (m, 2H), 3.26 (app. s, broad, 1H), 2.50 (s, 3H), 1.21 (t, J=7.0 Hz, 3H).

Workup

  1. customthe organic phase collected
  2. extractionThe aqueous layer was extracted with DCM (2×30 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue (5.5 grams) was used in the next reaction without further purification

Sources & evidence

ORD record
ord-8d23ceb657ff49abaec385a4181f9f48
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

Loading…