Реакция #828849

Уравнение реакции

3-(tert-butyldiphenylsilyloxymethyl)-1,6-dibromohexane

(S)-(-)-3-(tertbutyldiphenylsilyloxymethyl)-1,6-hexanediol

N-bromosuccinimide

triphenylphosphine

→

(S)-(-)-3-(tert-butyldiphenylsilyloxymethyl)-1,6-dibromohexane

Выход 75.0%

Условия реакции

Методика

Following the same procedure described for the preparation of racemic dibromide, 3-(tert-butyldiphenylsilyloxymethyl)-1,6-dibromohexane, (S)-(-)-3-(tertbutyldiphenylsilyloxymethyl)-1,6-hexanediol (4.85 g, 12.53 mmol) was reacted with N-bromosuccinimide (5.35 g, 30.1 mmol) and triphenylphosphine (7.87 g, 30.1 mmol) CH2Cl2 (150 mL) at 0° C. to afford compound (S)-(-)-3-(tert-butyldiphenylsilyloxymethyl)-1,6-dibromohexane 4.81 (75%) as a clear, colorless oil which was homogenous by TLC (Rf=0.8, 10% EtOAc in hexanes. Both the TLC properties and 1H spectra of this compound were identical in all respects with racemic isomer. MS.

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