Ammonium Chloride → 5-Fluoro-1-(methoxymethylidene)-2,3-dihydro-1H-indene-4-carbonitrile

HRID 2173245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2173245
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[F:29][C:30]1[CH:38]=[CH:37][C:36]2[C:35](=O)[CH2:34][CH2:33][C:32]=2[C:31]=1[C:40]#[N:41].[NH4+].[Cl-]>C1COCC1>[F:29][C:30]1[CH:38]=[CH:37][C:36]2[C:35](=[CH:2][O:3][CH3:4])[CH2:34][CH2:33][C:32]=2[C:31]=1[C:40]#[N:41]

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 552745775-fluoro-1-oxo-2,3-dihydro-1H-indene-4-carbonitrileHCID 178418339Butyllithium

Produkt 1

HCID 1317329685-Fluoro-1-(methoxymethylidene)-2,3-dihydro-1H-indene-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of (METHOXYMETHYL)TRIPHENYLPHOSPHONIUM CHLORIDE (1.3 g, 3.8 mmol) in THF (15 ml) was dropped n-Butyl Lithium (3.85 ml, 3.85 mmol) at −20° C. The mixture was stirred for 20 minutes before a THF solution of 5-Fluoro-1-oxo-2,3-dihydro-1H-indene-4-carbonitrile (450 mg, 2.6 mmol) was added into the reaction. TLC showed some green color spot right away. The reaction was then poured into NH4Cl, extracted with EtOAc, and flashed through silica gel. LC-MS (1E, m/z): 204 [M+1]+.

Aufarbeitung

  1. additionwas added into the reaction
  2. extractionextracted with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-06ee60df70de452eaf2f11131a590465
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056859B2

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