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2-Bromo-1-methoxy-4-(trifluoromethyl)benzene → HCID 57132321, Verbindung

HRID 1417548
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1417548
Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[O:12][CH3:13].C([Li])(C)(C)C.[CH2:19]([O:26][CH2:27][C@H:28]1[CH2:37][CH2:36][C@:30]2([O:34][CH2:33][C:32](=[O:35])[CH2:31]2)[C@@H:29]1[C:38]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[CH2:19]([O:26][CH2:27][C@H:28]1[CH2:37][CH2:36][C@:30]2([O:34][CH2:33][C@@:32]([OH:35])([C:2]3[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=3[O:12][CH3:13])[CH2:31]2)[C@@H:29]1[C:38]1[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 27570332-Bromo-1-methoxy-4-(trifluoromethyl)benzeneHCID 67671832HCID 67671832, VerbindungHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 57132321HCID 57132321, VerbindungAusbeute 51,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

2-Bromo-4-(trifluoromethyl)anisole (227 mg, 0.89 mmol), prepared according to the procedure of J. Alexander (Org. Prep. Proced. Int., 1986, 18, 213-215), was dissolved in 3.7 mL of THF and cooled in a -78° C. bath. A solution of t-butyllithium (1.0 mL, 1.7M in hexane, 1.7 mmol) was added over a period of 2 min. After 30 min., a solution of 200 mg (0.56 mmol) of (5R,6S,7S)-7-(benzyloxymethyl)-6-(4-fluorophenyl)-1-oxaspiro[4.4]nonane-3-one (prepared from methyl (5R,6S,7S)-6-(4-fluorophenyl)-3-(methylene)-1-oxaspiro[4.4]nonane-7-carboxylate (from Example 9) by DIBALH reduction, benzylation with sodium hydride and benzyl bromide, and oxidation as described in Example 6, Step C) in 1.0 mL of THF was added, and the reaction was stirred for 45 min. at -78° C. followed by warming to -35° C. over 20 min. The reaction was quenched by the addition of 10 mL of saturated aqueous ammonium chloride and partioned between 30 mL of ethyl acetate and 10 mL of water. The organic layer was washed with 10 mL of saturated aqueous sodium bicarbonate and 10 mL of saturated aqueous sodium chloride, dried over sodium sulfate, decanted, and evaporated. The crude product was purified by flash column chromatography, eluting with 1.5-5% ethyl ether in toluene to give 154 mg of the title compound.

Aufarbeitung

  1. temperatureby warming to -35° C. over 20 min
  2. customThe reaction was quenched by the addition of 10 mL of saturated aqueous ammonium chloride
  3. washThe organic layer was washed with 10 mL of saturated aqueous sodium bicarbonate and 10 mL of saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. customdecanted
  6. customevaporated
  7. customThe crude product was purified by flash column chromatography
  8. washeluting with 1.5-5% ethyl ether in toluene

Quellen und Nachweise

ORD-Eintrag
ord-97c2f75ca48b41cea8624972fc8fbecf
Quelldatensatz
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05877191

Notizen zur Reaktion

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