Diiodomethane → HCID 57684698, compound

Participants

Reaction Steps

To a cooled (0° C.) solution of ZnEt2 (0.16 mL, 0.16 mmol) in CH2Cl2 (0.4 mL) was added a solution of TFA (12 μL, 0.16 mmol) in CH2Cl2 (0.2 mL). After stirring for 20 min, a solution of CH2I2 (43 mg, 0.16 mmol) in CH2Cl2 (0.2 mL) was added. After stirring for an additional 20 min, a solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(3-methoxyprop-1-en-2-yl)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (intermediate BC) (32 mg, 0.053 mmol) in CH2Cl2 (0.4 mL) was added. The mixture was stirred overnight prior to quenching with a saturated solution of NaHCO3. The mixture was extracted 3× with CH2Cl2, and the organic portion was washed with brine prior to drying over Na2SO4. Concentration of the solution gave crude intermediate BC (25 mg).

Provenance & Evidence