Imidazole → Ethyl (S)-(-)-2-(tert-butyldimethylsilyloxy)propionate

HRID 78995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 78995
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C@H:2]([CH3:4])[OH:3].N1C=CN=C1.[CH3:14][C:15]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])[CH3:16]>C(Cl)Cl.O>[CH2:7]([O:6][C:1](=[O:5])[C@@H:2]([O:3][Si:18]([C:15]([CH3:17])([CH3:16])[CH3:14])([CH3:20])[CH3:19])[CH3:4])[CH3:8]

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 92831(L)-ethyl lactate

Produkt 1

HCID 10966394Ethyl (S)-(-)-2-(tert-butyldimethylsilyloxy)propionateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S)-(−)-ethyl lactate (37.4 g, 0.32 mol) in DCM (200 mL) was added imidazole (25.75 g, 0.38 mol) and TBSCl (50 g, 0.33 mol). The reaction mixture was stirred at room temperature for 2 hours. The reaction was diluted with water and extracted with DCM (2×50 mL), the combined organic extracts washed with brine dried (MgSO4) and concentrated in vacuo to give the title product as a colourless oil (100%). 1H NMR (CDCl3, 400 MHz) 4.21 (1 H, q, J=6.73 Hz), 4.14-4.01 (2H, m), 1.29 (3H, d, J=6.79 Hz), 1.18 (3H, t, J=7.09 Hz), 0.80 (9H, s), −0.01 (6H, s).

Aufarbeitung

  1. extractionextracted with DCM (2×50 mL)
  2. washthe combined organic extracts washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6a37e5b6d32240e9bdb28c03dcac8382
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841462B2

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