Merck 60 uv254 silica gel plates

Ergocalciferol was purchased from variable commercial sources (Alfa Aesar J62163, AstaTech 44109, Research Products International C20300, Sigma-Aldrich 95220, VWR 101172-472). ((Z)-2-((3S,5R)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-methylenecyclohexylidene) ethyl) diphenylphosphine oxide was purchased from ChemScene (CS-M0003). All moisture or oxygen-sensitive reactions were carried out under a dry nitrogen atmosphere. Reaction temperatures refer to the containing bath temperatures. Reactions were monitored by thin-layer chromatography (TLC) using Merck 60 UV254 silica gel plates (Sigma-Aldrich). Visualization was performed with UV light, cerium molybdate general stain followed by heating, and other methods as noted. Synthesized compounds were purified by normal phase flash chromatography (SPI Biotage, silica gel 230-400 mesh) except where noted. Compound characterization was performed via Shimadzu 2020 LC-MS (single quadrupole) instrument. NMR spectra were recorded on a Bruker Avance 500MHz instrument with compounds dissolved in the specified deuterated solvent. Optical rotations were recorded using Jasco DIP-370 Digital Polarimeter instrument in LCMS grade chloroform or methanol.

Ergocalciferol was purchased from AstaTech (44109). ((Z)-2-((3S,5R)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-methylenecyclohexylidene)ethyl) diphenylphosphine oxide was obtained from ChemScene (CS-M1835). All moisture or oxygen-sensitive reactions were carried out under a dry nitrogen atmosphere. All reactions were monitored by thin-layer chromatography (TLC) using Merck 60 UV254 silica gel plates (Sigma-Aldrich). Products were purified by flash chromatography (SPI Biotage, silica gel 230–400 mesh). Compound masses were identified using a Shimadzu 2020 LC-MS (single quadrupole) instrument. NMR spectra were recorded on a Bruker Avance 500 MHz instrument. Optical rotations were recorded using Jasco DIP-370 Digital Polarimeter instrument in LCMS grade chloroform or methanol.