Triethylamine → (E)-4-(2-methyl-benzothiazol-6-yl)-but-3-enoic acid methyl ester

HRID 881886

Reaktionsgleichung

Reaktionsgleichung von HRID 881886
I[C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([CH3:9])[S:8][C:4]=2[CH:3]=1.[CH3:12][O:13][C:14](=[O:18])[CH2:15][CH:16]=[CH2:17].C(N(CC)CC)C>C(O[Pd]OC(=O)C)(=O)C>[CH3:12][O:13][C:14](=[O:18])[CH2:15]/[CH:16]=[CH:17]/[C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([CH3:9])[S:8][C:4]=2[CH:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 77314Methyl 3-butenoateHCID 8075926-Iodo-2-methyl-1,3-benzothiazole

Produkt 1

HCID 67505910(E)-4-(2-methyl-benzothiazol-6-yl)-but-3-enoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 167845palladium(II) acetateKatalysator

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 6-iodo-2-methylbenzo[d]thiazole (275 mg, 1 mmol), but-3-enoic acid methyl ester (100 mg, 1.2 mmol), diacetoxypalladium (22 mg, 0.1 mmol) and triethylamine (304 mg, 3 mmol) MeCN (8 mL) is heated in a microwave apparatus at 130° C. for 30 minutes. The solvent is removed under reduce pressure and the residue is purified by flash chromatography (heptane:EtOAc, 2:1) to give (E)-4-(2-methyl-benzothiazol-6-yl)-but-3-enoic acid methyl ester. MS 248.3 (M+1).

Aufarbeitung

  1. customThe solvent is removed
  2. customthe residue is purified by flash chromatography (heptane:EtOAc, 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-2a3f1c955a9747068aef64fbe92f7eb1
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993631B2

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