1-Iodoheptane → Ethyl 4-[(4,4-dimethyl-2-heptylthio-3,4-dihydro-6-quinolinyl)ethynyl]benzoate

HRID 52440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 52440
[H-].[Na+].I[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]C.[CH3:11][C:12]1([CH3:37])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]#[C:23][C:24]3[CH:34]=[CH:33][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=3)[CH:20]=2)[N:15]=[C:14]([S:35][CH3:36])[CH2:13]1>C1COCC1>[CH3:37][C:12]1([CH3:11])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]#[C:23][C:24]3[CH:34]=[CH:33][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=3)[CH:20]=2)[N:15]=[C:14]([S:35][CH2:36][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH2:13]1

Komponenten

5

Edukt 3

HCID 202741-IodoheptaneHCID 24758Sodium hydrideHCID 19963703Ethyl 4-[(4,4-dimethyl-2-methylthio-3,4-dihydro-6-quinolinyl)ethynyl]benzoate2×

Produkt 1

HCID 19963725Ethyl 4-[(4,4-dimethyl-2-heptylthio-3,4-dihydro-6-quinolinyl)ethynyl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

0.025 g (0.694 mmol) of sodium hydride in 2 ml of THF, 0.229 g (0.631 mmol) of ethyl 4-[(4,4-dimethyl-2-thio-1,2,3,4-tetrahydro-6-quinolinyl)ethynyl]benzoate (Compound 8) in 2 ml of THF and 1.03 ml (6.31 mmol) of iodoheptane were reacted substantially in accordance with the procedure used for the preparation of ethyl 4-[(4,4-dimethyl-2-methylthio-3,4-dihydro-6-quinolinyl)ethynyl]benzoate (Compound 9). Purification by flash chromatography (silica gel, 10% ethyl acetate in hexane) yielded the title compound as a yellow solid.

Aufarbeitung

  1. customPurification by flash chromatography (silica gel, 10% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-f4eb101334c14f498b6ce499940c861b
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616712

Notizen zur Reaktion

Wird geladen…