Water → (S)-1-(tert-butyldimethylsilyloxy)-3-(hexadecyloxy)propan-2-ol

HRID 2204969Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2204969
[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]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 11758911(2R)-3-(Hexadecyloxy)-1,2-propanediol

Produkt 1

HCID 10960980(S)-1-(tert-butyldimethylsilyloxy)-3-(hexadecyloxy)propan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  1. extractionthe aqueous phase was back extracted with DCM
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated en vaccuo
  5. customThe resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Quellen und Nachweise

ORD-Eintrag
ord-203199c6a65d40da9b6b9e8a08d9731e
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365506B2

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