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3,3-Dimethylbutanoyl chloride → Methyl 3-[3-(3,3-dimethyl-1-oxo-1-butyl)-5-(quinolin-2-ylmethoxy)indol-2-yl]-2,2-dimethyl-propanoate

HRID 327244
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 327244
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][C:6]([CH3:12])([CH3:11])[CH2:7][C:8](Cl)=[O:9].[N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[CH2:23][O:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29]([CH2:34][C:35]([CH3:41])([CH3:40])[C:36]([O:38][CH3:39])=[O:37])=[CH:28]2.C(C(C(C([O-])=O)O)O)([O-])=O>C(Cl)Cl>[CH3:5][C:6]([CH3:12])([CH3:11])[CH2:7][C:8]([C:28]1[C:27]2[C:31](=[CH:32][CH:33]=[C:25]([O:24][CH2:23][C:14]3[CH:15]=[CH:16][C:17]4[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:13]=3)[CH:26]=2)[NH:30][C:29]=1[CH2:34][C:35]([CH3:41])([CH3:40])[C:36]([O:38][CH3:39])=[O:37])=[O:9]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 815143,3-Dimethylbutanoyl chlorideHCID 38061142,3-DihydroxybutanedioateHCID 6451240Aluminum(III) ChlorideHCID 18947552Methyl 3-[5-(quinolin-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoate

Produkt 1

HCID 18947551Methyl 3-[3-(3,3-dimethyl-1-oxo-1-butyl)-5-(quinolin-2-ylmethoxy)indol-2-yl]-2,2-dimethyl-propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of AlCl3 (5.7 g, 42 mmol) in CH2Cl2 (30 mL) at 0° C. was added 3,3-dimethylbutanoyl chloride (2.4 mL. 17 mmol). After 15 minutes at 0° C., a solution of the ester from step C (3.0 g, 7.7 mmol) in CH2Cl2 (10 mL) was added by double-tipped needle. The mixture was stirred a further 20 minutes, at which point it was poured into a mixture of 0.5M Na, K tartrate (150 mL) and ice (100 g). The product was extracted with EtOAc, and the organic layer was washed successively with 0.5M NaK tartrate, H2O, and brine. The solvent was then removed and yellow/orange oil (3.5 g) was used without purification in the following step.

Aufarbeitung

  1. extractionThe product was extracted with EtOAc
  2. washthe organic layer was washed successively with 0.5M NaK tartrate, H2O, and brine
  3. customThe solvent was then removed
  4. customyellow/orange oil (3.5 g) was used without purification in the following step

Quellen und Nachweise

ORD-Eintrag
ord-4cf50b56211a4dc09b1bc0e15b3f5056
Quelldatensatz
uspto-grants-1993_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05272145

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