LitCovid-sentences  

PMC:7291971 / 79477-81147 JSONTXT 7 Projects

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Id Subject Object Predicate Lexical cue
T529 0-200 Sentence denotes To a solution of 20 (210 mg, 0.25 mmol, 1.00 eq) in anhydrous DCE (7 mL) was added 4-chlorobenzaldehyde (43 mg, 0.38 mmol, 1.50 eq) in anhydrous DCE (7 mL) and acetic acid (18 μL, 0.38 mmol, 1.50 eq).
T530 201-316 Sentence denotes After stirring for 20 min at 40 °C under argon, sodium triacetoxyborohydride (81 mg, 0.38 mmol, 1.50 eq) was added.
T531 317-434 Sentence denotes After stirring at 40 °C for 16 h, the solution was diluted with DCM (50 mL) and washed with saturated aqueous NaHCO3.
T532 435-602 Sentence denotes The aqueous layer was extracted with DCM (3 × 50 mL) and the combined organic extracts were washed with brine (70 mL), dried over Na2SO4 and concentrated under vacuum.
T533 603-759 Sentence denotes The residue was purified by flash column chromatography (silica gel, linear gradient 0–5% MeOH in DCM) to give 36 as a white solid (172 mg, 0.18 mmol, 72%).
T534 760-787 Sentence denotes Rf 0.71 (MeOH/CH2Cl2 5:95).
T535 788-1321 Sentence denotes 1H NMR (600 MHz, CDCl3) δ 8.30 (s, 1H), 8.20 (s, 1H), 8.15 (s, 1H), 7.83 (s, 1H), 7.19–7.07 (m, 4H), 6.11 (d, J = 3.7 Hz, 1H), 5.99 (d, J = 2.2 Hz, 1H), 5.97–5.83 (m, 4H), 5.37 (dd, J = 6.5 Hz, J = 2.2 Hz, 1H), 4.85 (dd, J = 6.4 Hz, J = 3.4 Hz, 1H), 4.49 (t, J = 5.1 Hz, 1H), 4.32 (td, J = 6.7 Hz, J = 3.3 Hz, 1H), 4.26 (t, J = 4.2 Hz, 1H), 4.08 (dt, J = 5.9 Hz, J = 3.1 Hz, 1H), 3.98 (dd, J = 11.5 Hz, J = 3.6 Hz, 1H), 3.79–3.47 (m, 5H), 2.84–2.66 (m, 4H), 1.58 (s, 3H), 1.36 (s, 3H), 0.92 (s, 9H), 0.88 (s, 9H), 0.13–0.02 (m, 12H).
T536 1322-1591 Sentence denotes 13C NMR (150 MHz, CDCl3) δ 155.7, 155.6, 153.1, 153.1, 149.7, 149.3, 140.0, 139.5, 137.8, 132.8, 130.1, 128.4, 120.5, 120.3, 114.4, 91.0, 87.2, 85.7, 84.9, 84.0, 83.5, 82.7, 69.8, 69.5, 61.3, 58.6, 56.4, 53.6, 27.3, 26.2, 25.9, 25.5, 18.6, 18.2, −4.5, −4.7, −5.2, −5.3.
T537 1592-1643 Sentence denotes HRMS (ESI+): m/z calcd for C44H67N11O7Si2Cl [M+H]+:
T538 1644-1660 Sentence denotes 952.4447, found:
T539 1661-1670 Sentence denotes 952.4426.