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Diisopropylamine → Tert-butyl 6-triphenylmethyloxy-5-hydroxy-3-oxohexanoate

HRID 1594449
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1594449
C(NC(C)C)(C)C.[Li]CCCC.[C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH3:14].[C:21]1([C:27]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[O:28][CH2:29][CH:30]([OH:36])[CH2:31][C:32](OC)=[O:33])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1.O>[C:21]1([C:27]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[O:28][CH2:29][CH:30]([OH:36])[CH2:31][C:32](=[O:33])[CH2:14][C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 7912DiisopropylamineHCID 10908tert-Butyl acetateHCID 11245840Methyl 4-triphenylmethyloxy-3-hydroxybutyrateHCID 178418339Butyllithium

Produkt 1

HCID 19778647Tert-butyl 6-triphenylmethyloxy-5-hydroxy-3-oxohexanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

125 mL of THF and 24 g of diisopropylamine were charged and cooled to −15° C. 168 mL of 1.2 N n-BuLi was added at −15 to −5° C. and was stirred for 30 minutes. 21.56 g of tert-butyl acetate in 45 mL of THF, which was pre-cooled to −45° C., was added maintaining the temperature between −45 to −25° C. for 60 minutes. The reaction mixture was cooled to −45° C. and 30 g of methyl 4-triphenylmethyloxy-3-hydroxybutyrate in THF was added over a period of 20 minutes and the stirring was continued at −25° C. for 90 minutes. Water was added and the layers were separated. The aqueous layer was extracted using EtOAc and the combined organic layers were washed with brine, water, dried and concentrated to give the title compound which was used as such for the next step.

Aufarbeitung

  1. additionwas added
  2. temperaturemaintaining the temperature between −45 to −25° C. for 60 minutes
  3. temperatureThe reaction mixture was cooled to −45° C.
  4. waitthe stirring was continued at −25° C. for 90 minutes
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted
  7. washthe combined organic layers were washed with brine, water
  8. customdried
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-04ab3f28f6c54b82810e23f863f9d1f3
Quelldatensatz
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07301046B2

Notizen zur Reaktion

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