Reaktion #2288

Reaktionsgleichung

product

[2-(1-Naphthyl)-6-methoxybenzothien-3-yl][4-[2-(1-piperdinyl)ethoxy]phenyl]methanone

ethanethiol

aluminum chloride

→

title product

Ausbeute 53.4%

[2-(1-Naphthyl)-6-hydroxybenzothien-3-yl][4-[2-(1-piperdinyl)ethoxy]phenyl]methanone

Ausbeute 53.4%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was quenched with saturated potassium sodium tartrate (
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   WaschenThe organic layer was washed with saturated sodium potassium tartrate and brine
4. 4
   Trocknendried (sodium sulfate)
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was purified by chromatography (silica gel, 0-10% methanol in methylene chloride)

Vorschrift

A solution of the product of Example 1 (1.00 g, 1.92 mmol), ethanethiol (0.45 mL, 6.18 mmol), and aluminum chloride (1.54 g, 11.55 mmol) in anhydrous methylene chloride (40 mL) was stirred for 3.5 hours. The mixture was quenched with saturated potassium sodium tartrate (also known as Rochelle's salt) and extracted with ethyl acetate. The organic layer was washed with saturated sodium potassium tartrate and brine, dried (sodium sulfate), and concentrated. The residue was purified by chromatography (silica gel, 0-10% methanol in methylene chloride) to give 520 mg (53%) of the title product as a dark yellow/green foam: 1H NMR (300 MHz, CDCl3) δ1.46 (m, 2H), 1.65 (m, 4H), 2.54 (m, 4H), 2.73 (t, J=5.4 Hz, 2H), 3.96 (t, J=5.4 Hz, 2H), 6.37 (d, J=8.7 Hz, 2H), 6.88 (dd, J=1.9 Hz, 8.8 Hz, 1H), 7.23-7.29 (m, 2H), 7.37-7.51 (m, 5H), 7.62-7.70 (m, 3H), 8.02-8.05 (m, 1H), 8.28 (br s, 1H); 13C NMR (75 MHz, CDCl3) δ23.3, 24.7, 54.4, 57.0, 64.5, 106.9, 113.0, 115.2, 124.2, 124.3, 125.2, 125.5, 126.1, 127.6, 128.7, 128.7, 130.3, 130.5, 131.2, 131.6, 131.8, 132.8, 133.4, 140.7, 141.1, 154.6, 161.6, 192.1; MS (FD) m/e 508 (MH+); Anal. calc'd. for C32H29NO3S: C, 75.71; H, 5.76; N, 2.76. Found: C, 75.43; H, 6.02; N, 3.03.

Quelle