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Water → 4-({5-[(4-Fluorophenyl)carbonyl]-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridin-2-yl}methoxy)phenol

HRID 1529580
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1529580
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C:27]1[CH:52]=[CH:51][C:30]([O:31][CH2:32][C:33]2[O:34][C:35]3[CH2:36][N:37]([C:42]([C:44]4[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=4)=[O:43])[CH2:38][CH2:39][C:40]=3[N:41]=2)=[CH:29][CH:28]=1)(C(C)(C)C)(C)C.O>C1COCC1>[F:50][C:47]1[CH:48]=[CH:49][C:44]([C:42]([N:37]2[CH2:38][CH2:39][C:40]3[N:41]=[C:33]([CH2:32][O:31][C:30]4[CH:29]=[CH:28][C:27]([OH:26])=[CH:52][CH:51]=4)[O:34][C:35]=3[CH2:36]2)=[O:43])=[CH:45][CH:46]=1
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Komponenten

5

Edukt 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 666088752-[(4-{[Tert-butyl(dimethyl)silyl]oxy}phenoxy)methyl]-5-[(4-fluorophenyl)carbonyl]-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridine

Produkt 1

HCID 569416354-({5-[(4-Fluorophenyl)carbonyl]-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridin-2-yl}methoxy)phenolAusbeute 45,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

1M solution of tetra-butylammonium fluoride in THF (0.54 mL, 0.54 mmol) was added to a stirred solution of 2-[(4-{[tert-butyl(dimethyl)silyl]oxy}phenoxy)methyl]-5-[(4-fluorophenyl)carbonyl]-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridine (264 mg, 0.36 mmol) in THF (2 mL). The mixture was stirred at room temperature for 16 hours. The mixture was treated with water and extracted with AcOEt. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 100/0). The desired fractions were collected and the solvents evaporated in vacuo. The product was triturated with DIPE to yield (4-({5-[(4-fluorophenyl)carbonyl]-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridin-2-yl}methoxy)phenol (60 mg, 45% yield) as a white solid. C20H17FN2O4 1H NMR (400 MHz, CDCl3) δ ppm 2.72 (br. s., 2 H), 3.69 (br. s, 2 H), 4.78 (br.s., 2 H), 5.05 (br. s., 2 H), 5.86 (br. s., 1 H), 6.74 (d, J=8.8 Hz, 2 H), 6.86 (d, J=8.8 Hz, 2 H), 7.09-7.18 (m, 2 H), 7.43-7.51 (m, 2 H).

Aufarbeitung

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo
  6. customThe crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 100/0)
  7. customThe desired fractions were collected
  8. customthe solvents evaporated in vacuo
  9. customThe product was triturated with DIPE

Quellen und Nachweise

ORD-Eintrag
ord-86e94b8779e9411ab76942d9053b7726
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09090632B2

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