3-(苯基巯基)丙烷-1-醇

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 3-(Phenylthio)-1-propanol (3.00 g), 1,6-dibromohexane (5.5 ml), aqueous 12.5M sodium hydroxide (27 ml) and TAB (802 mg) were vigorously stirred at room temperature overnight. The mixture was diluted with water (60 ml), extracted with diethyl ether (3×90 ml), and the combined, dried organic extracts were evaporated. The residual oil was purified by FCC eluting with System B (1:99→1:24) to give the title compound (4.01 g) as a colourless oil. T.l.c. (System B 1:3) Rf 0.35. extracted with diethyl ether (3×90 ml) dried organic extracts were evaporated The residual oil was purified by FCC eluting with System B (1:99→1:24)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Diethyl azodicarboxylate (14 ml, 89 mmol) was added over 3 minutes to a stirred solution of 3-phenylthiopropanol (14.91 g, 89 mmol), triphenylphosphine (23.25 g, 89 mmol) and phthalimide (13.05 g, 89 mmol) in tetrahydrofuran (350 ml) at room temperature. After 15 hours, the mixture was concentrated in vacuo. Flash chromatography of the residue, eluting with 1:1 ether/hexane, gave the title compound as a white solid (22.5 g 85%). NMR (200 MHz, CDCl3): δ 2.0 (q, 2H), 2.95 (t, 2H), 3.85 (t, 2H), 7.25 (m, 5H), 7.8 (m, 4H). the mixture was concentrated in vacuo Flash chromatography of the residue, eluting with 1:1 ether/hexane