Reaktion #1079773

Reaktionsgleichung

Tert-butyldiphenylsilyl chloride

Pentaerythritol

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product

Ausbeute 133.4%

2-(Hydroxymethyl)-2-[(1,1,2,2-tetramethyl-1-silapropoxy)methyl]propane-1,3- diol

Ausbeute 133.4%

Lösungsmittel

EtOAc

EtOAc

pyridine

EtOAc

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashing the organic layer with 10% HCl (3×200 mL)
2. 2
   TrocknenThe organic layer was dried over sodium sulfate
3. 3
   Einengenconcentrated in vacuo
4. 4
   Sonstigeto afford a thick pale yellow oil

Vorschrift

Pentaerythritol [2,2-bis(hydroxymethyl)propane-1,3-diol] (10.55 g, 77 mmol) was taken up in 100 mL of dry pyridine. Tert-butyldiphenylsilyl chloride (4.26 g, 15 mmol, 0.2 eq) was then added dropwise over 10 minutes to the pyridine solution at ambient temperature. The reaction mixture was stirred at ambient temperature for 24 hours at which point TLC (EtOAc) indicated that the reaction was complete. The reaction was worked-up by diluting the reaction mixture with 250 mL of EtOAc and washing the organic layer with 10% HCl (3×200 mL). The organic layer was dried over sodium sulfate and then concentrated in vacuo to afford a thick pale yellow oil. Column chromatography on 200 g of silica gel eluting with EtOAc followed by concentration of the appropriate fractions afforded 5.01 g of the product as a clear colorless oil which solidified very slowly upon standing (86%). 1H NMR (CDCl3, 300 MHz): δ1.08 (s, 9H), 3.66 (s, 2H), 3.74 (s, 6H), 7.42 (m, 6H), 7.65 (m, 4H); MS (70 eV, EI) 392 (M+NH4)+.

Quelle