Tetrahydrofuran → HCID 77985821, compound

Participants

Reaction Steps

To a flame-dried 20 mL vial fitted with a screw-top septa cap was charged with dimethyl 3,4-bis(8-(acetylthio)octyl)hexanedioate (1 equiv, 0.34 mmol, 187 mg, mixture of stereoisomers) and THF (4.5 mL). DIBAl-H (12 equiv, 4.1 mmol, 2.7 mL of a nominally 1.5 M solution in toluene) was added dropwise. The reaction was stirred for 3 h at rt, quenched by careful addition of 2 N HCl (5 mL), diluted with 10 mL sat. aq. NH4Cl (10 mL), and extracted with Et2O (3×15 mL). The combined organic layers were washed with brine (1×15 mL), dried with Na2SO4, concentrated in vacuo, and purified by flash column chromatography (35% EtOAc/Hex) to afford rac-3,4-Bis(8-mercaptooctyl)hexane-1,6-diol (41 mg, 30%) and meso-3,4-Bis(8-mercaptooctyl)hexane-1,6-diol (49 mg, 49%). TLC rac-Rf=0.57 (50% EtOAc/Hex), meso-Rf=0.38 (50% EtOAc/Hex); rac: 1HNMR (400 MHz): δ 3.60-3.79 (4H), 2.54 (q, 4H, J=7.3 Hz), 1.14-1.68 (38H); 13CNMR (100 MHz): δ 61.6, 35.8, 34.0, 33.7, 30.7, 30.0, 29.5, 29.1, 28.3, 28.0, 24.6; FTIR: 3323, 2922, 2852, 1463, 1051, 722 cm−1; HRMS-ESI: calc. for C22H46NaO2S2 (M+Na)+: 429.2837. found: 429.2825; meso: 1HNMR (400 MHz): δ 3.59-3.76 (4H), 2.54 (q, 4H, J=7.3 Hz), 1.87 (bs, 2H), 1.08-1.68 (36H); 13CNMR (100 MHz): δ 61.9, 36.7, 34.0, 33.8, 30.7, 30.0, 29.5, 29.1, 28.4, 28.0, 24.7; FTIR: 3329, 2922, 2852, 1463, 1051, 721 cm−1; HRMS-ESI: calc. for C22H46NaO2S2 (M+Na)+: 429.2837. found: 429.2829.

Provenance & Evidence