Water → (S)-1-(tert-butyldimethylsilyloxy)-3-(hexadecyloxy)propan-2-ol
Reaction equation
[CH2:1]([O:17][CH2:18][C@H:19]([OH:22])[CH2:20][OH:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH3:23][C:24]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])[CH3:25].CCN(CC)CC.O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Si:27]([O:21][CH2:20][C@@H:19]([OH:22])[CH2:18][O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])([C:24]([CH3:26])([CH3:25])[CH3:23])([CH3:29])[CH3:28]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
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.
Workup
- extractionthe aqueous phase was back extracted with DCM
- washThe combined organic phases were washed with brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated en vaccuo
- customThe resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO)
Sources & evidence
- ORD record
- ord-203199c6a65d40da9b6b9e8a08d9731e
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365506B2
Reaction notes
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