Perchloric Acid → (S)-ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-6-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate

HRID 514060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 514060
Cl(O)(=O)(=O)=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:22]3[C:17](=[CH:18][C:19]([O:23][S:24]([C:27]([F:30])([F:29])[F:28])(=[O:26])=[O:25])=[CH:20][CH:21]=3)[CH:16]=[C:15]([CH3:31])[C:14]=2[C@H:32]([OH:38])[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:9][CH:8]=1.C([O-])(O)=O.[Na+]>C(OC(C)(C)C)(=O)C>[C:10]([O:38][C@@H:32]([C:14]1[C:15]([CH3:31])=[CH:16][C:17]2[C:22](=[CH:21][CH:20]=[C:19]([O:23][S:24]([C:27]([F:30])([F:29])[F:28])(=[O:26])=[O:25])[CH:18]=2)[C:13]=1[C:10]1[CH:9]=[CH:8][C:7]([Cl:6])=[CH:12][CH:11]=1)[C:33]([O:35][CH2:36][CH3:37])=[O:34])([CH3:13])([CH3:11])[CH3:9]

Komponenten

5

Edukt 3

HCID 24247Perchloric AcidHCID 516892Sodium Bicarbonate2×HCID 86691546(S)-ethyl 2-(1-(4-chlorophenyl)-3-methyl-6-(trifluoromethylsulfonyloxy) naphthalen-2-yl)-2-hydroxyacetate

Produkt 1

HCID 86691548(S)-ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-6-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetateAusbeute 116,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10908tert-Butyl acetateLösungsmittel

Versuchsvorschrift

Perchloric acid (70%, 0.28 mL, 3.2 mmol) was added to a solution of (S)-ethyl 2-(1-(4-chlorophenyl)-3-methyl-6-(trifluoromethylsulfonyloxy) naphthalen-2-yl)-2-hydroxyacetate (0.82 g, 1.6 mmol) in tert-butyl acetate (5 mL) at room temperature. After 3 h, solid NaHCO3 was added and the slurry stirred vigorously for 30 min. Saturated NaHCO3 was added slowly until the mixture was pH ˜8. Following extraction of the organic layer with EtOAc, the combined organics were washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. The resulting residue was purified by Yamazen column chromatography (0-35% EtOAc/Hex) to produce 0.52 g (57%) of the title compound as an amorphous solid. 1H-NMR: 400 MHz, (CDCl3) δ: 7.69 (s, 1H); 7.66 (d, J=2.4 Hz, 1H); 7.51 (m, 2H); 7.44 (m, 1H); 7.34 (d, J=9.4 Hz, 1H); 7.27 (m, 1H); 7.15 (dd, J=9.4, 2.4 Hz, 1H); 5.12 (s, 1H); 4.17 (m, 2H); 2.63 (s, 3H); 1.23 (t, J=7.2 Hz, 3H); 1.01 (s, 9H).

Aufarbeitung

  1. extractionextraction of the organic layer with EtOAc
  2. washthe combined organics were washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by Yamazen column chromatography (0-35% EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-830b9125f629475c84cb7d29bb5b6adf
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102614B2

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