C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.O[CH2:33][CH2:34][CH:35]([CH2:39][CH2:40][OH:41])[CH2:36][CH2:37][OH:38].[C:42]([OH:45])(=[S:44])[CH3:43]>C1COCC1>[C:42]([S:44][CH2:33][CH2:34][CH:35]([CH2:39][CH2:40][OH:41])[CH2:36][CH2:37][OH:38])(=[O:45])[CH3:43]
To a solution of triphenylphosphine (1.77 g, 6.8 mmol) in anhydrous THF (15 mL) was added diethyl azodicarboxylate (2.2 M in toluene, 2.4 mL, 5.4 mmol) dropwise at 0° C. After stirred at 0° C. for 55 minutes, a solution of 3-(2-hydroxyethyl)pentane-1,5-diol (740 mg, 5 mmol) and thioacetic acid (335 μL, 4.5 mmol) in dry THF (7 mL) was added dropwise. After 1 hour the ice/water bath was removed and the reaction was stirred at room temperature for 16 hours. The solvents were removed by rotary evaporation in vacuo. The residue was purified by flash chromatography (CHCl3/MeOH, 20:1, 15:1, 10:1, 4:1) to give 3-(2-acetylthioethyl)pentane-1,5-diol as white solid (350 mg) and recovered starting material triol (406 mg). 1H NMR (400 Hz, CDCl3): δ 3.65-3.63 (m, 4H), 3.45 (bs, 2H), 2.84-2.80 (m, 2H), 2.28 (s, 3H), 1.73-1.67 (m, 1H), 1.55-1.49 (m, 6H). MS (ESI): m/z 229.0 (M+Na)+.
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