HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → (S)-1-(tert-butyldimethylsilyloxy)-3-(hexadecyloxy)propan-2-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | tert-Butyldimethylsilyl chloride | HCID 28928 | — |
| Reactant | (2R)-3-(Hexadecyloxy)-1,2-propanediol | HCID 11758911 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (S)-1-(tert-butyldimethylsilyloxy)-3-(hexadecyloxy)propan-2-ol | HCID 10960980 | — |
Reaction Steps
A solution of (R)-3-(hexadecyloxy)propane-1,2-diol (1 eq), TBDMSCl (1.4 eq), NEt3 (1.4 eq) and DMAP (0.05 eq) in DCM (0.5 M) was stirred at 25° C. over night. The reaction was diluted with DCM and was with H2O twice, and the aqueous phase was back extracted with DCM. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate and concentrated en vaccuo. The resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-20% EtOAc/Hex to give (S)-1-(tert-butyldimethylsilyloxy)-3-(hexadecyloxy)propan-2-ol as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09365506B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-203199c6a65d40da9b6b9e8a08d9731e |
| Source note | uspto-grants-2016_06 |