Compound 2a

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InChIKey QNTNIQRWTZVENI-WBIAXQAASA-L

Compound data: CIF

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

The compound, HC≡CCOOMe (67 μL, 0.80 mmol), was added to a suspension of compound 1 (300 mg, 0.27 mmol) in dichloromethane (15 mL). The mixture was stirred at room temperature for five minutes to give a yellow solution. The solution was evaporated under vacuum to a volume of approximately 2 mL and then purified by column chromatography (neutral alumina, eluent: dichloromethane/methanol = 20:1) to give a yellow solution. The yellow solid of 2a (258 mg, 80%) was collected after the solvent was evaporated to dryness under vacuum. ¹H-NMR plus ¹H-¹³C HSQC (500.1 MHz, CDCl₃): δ 14.25 (s, 1H, H⁷), 9.27 (s, 1H, H⁵), 8.32 (s, 1H, H³), 3.68 (s, 3H, COOCH₃), 7.87–6.93 ppm (m, 45H, other aromatic protons). ³¹P-NMR (202.5 MHz, CDCl₃): δ 6.54 (t, J_P-P = 4.9 Hz, CPPh₃), 3.75 ppm (d, J_P-P = 4.9 Hz, OsPPh₃). ¹³C-NMR plus DEPT-135 and ¹H-¹³C HSQC (125.8 MHz, CD₂Cl₂): δ 324.5 (td, J_P-C = 14.5 Hz, J_P-C = 13.6 Hz, C¹), 227.9 (br, C⁷), 182.0 (d, J_P-C = 22.8 Hz, C⁴), 163.2 (s, COOCH₃, confirmed by ¹H-¹³C HMBC), 158.5 (d, J_P-C = 15.2 Hz, C³), 155.6 (s, C⁶), 154.3 (s, C⁵), 119.1 (d, J_P-C = 90.9 Hz, C²), 51.6 (s, COOCH₃), 135.4–127.8 ppm (m, other aromatic carbons). HRMS (ESI): m/z calcd for [C₆₃H₅₁ClO₂OsP₃]⁺, 1159.2394; found, 1159.2404.