Toluene → ethyl 2-hydroxy-2-(1-methyl-3-phenyl-1H-indol-2-yl)acetate

HRID 590954

Reaktionsgleichung

Reaktionsgleichung von HRID 590954
C([Li])CCC.[CH3:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:8]1.[C:22]([O:26][CH2:27][CH3:28])(=[O:25])[CH:23]=[O:24].C1(C)C=CC=CC=1>O1CCCC1>[OH:24][CH:23]([C:8]1[N:7]([CH3:6])[C:15]2[C:10]([C:9]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:22]([O:26][CH2:27][CH3:28])=[O:25]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 70211Ethyl oxoacetateHCID 6101761-Methyl-3-phenylindoleHCID 178418339Butyllithium

Produkt 1

HCID 70813741ethyl 2-hydroxy-2-(1-methyl-3-phenyl-1H-indol-2-yl)acetateAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of butyllithium (1.6 M, 3.44 mL, 5.5 mmol) was added at −20° C. to a solution of 1-methyl-3-phenyl-1H-indole (1b) (1.08 g, 5.3 mmol) in anhydrous tetrahydrofuran (20 mL) under a nitrogen atmosphere. After 1 hour, a solution of ethyl glyoxylate in toluene (50%, 1.1 mL, 5.5 mmol) was added. The reaction mixture was slowly warmed to room temperature for 2 hours, quenched with water (5 mL) and concentrated in vacuo. The residue was partitioned between dichloromethane (40 mL) and water (15 mL). The organic layer was washed with water (2×15 mL), brine (15 mL), dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired alcohol (1c) as a white solid (360 mg, 1.16 mmol, 22%).

Aufarbeitung

  1. customquenched with water (5 mL)
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between dichloromethane (40 mL) and water (15 mL)
  4. washThe organic layer was washed with water (2×15 mL), brine (15 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10)

Quellen und Nachweise

ORD-Eintrag
ord-a240b766312c4329a26c1b3ed43fb300
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238026B2

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