Tetrahydrofuran → HCID 71477884, compound

Participants

Reaction Steps

To a flamed-dried 20 mL vial fitted with a screw-cap septa was added Dimethyl 3,4-bis(8-(acetylthio)octyl)hex-3-enedioate (1 equiv, 0.36 mmol, 196 mg) and THF (4.5 mL). DIBAl-H (12 equiv, 4.3 mmol, 2.9 mL of a nominally 1.5 M solution in toluene) was added dropwise at rt. The reaction was stirred at rt for 2 h and quenched by the careful addition of 2N HCl (3 mL). The solution was transferred to a sepratory funnel and diluted with sat. aq. NH4Cl (15 mL) and Et2O (15 mL). The layers were separated and the aqueous layer extracted with Et2O (2×15 mL). The combined organic layers were washed with brine (20 mL), dried with Na2SO4, concentrated in vacuo, and purified by flash column chromatography (40% EtOAc/Hex) to afford (Z)-3,4-bis(8-mercaptooctyl)hex-3-ene-1,6-diol (82.8 mg, 0.205 mmol, 57%). TLC Rf=0.41 (50% EtOAc/Hex); Mp=67.4-68.2° C.; 1HNMR (600 MHz): δ 3.64 (t, 4H, J=6.9 Hz), 2.54 (q, 4H, J=7.4 Hz), 2.35 (t, 4H, J=7.0 Hz), 2.08-2.02 (4H), 1.68 (bs, 2H), 1.62 (quint., 4H, J=7.4 Hz), 1.42-1.27 (22H); 13CNMR (150 MHz): δ 132.4, 61.3, 34.6, 34.0, 31.7, 29.7, 29.5, 29.2, 29.0, 28.3, 24.6; FTIR: 3402, 3349, 2923, 2850, 1465, 1348, 1028, 721 cm−1; HRMS-ESI: calc. for C22H44NaO2S2 (M+Na)+: 427.2680. found: 427.2679.

Provenance & Evidence