Ammonium Chloride → HCID 14758908, compound

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Reaction Steps

With stirring, 4,4′-di-tert-butyl biphenyl (3.6 g) under an Argon atmosphere is added at 0° C. to a suspension of lithium (30% in mineral oil) in THF (30 ml). Stirring is continued for 2 h at r.t. The resulting deep green solution is added dropwise to a solution of (S)-1-benzyloxy-5-(ter-butyldimethylsilyloxy)-4-methyl-pentane 5 (673 mg, 2.09 mmol) in 10 ml of THF at −78° C., until the colour of the mixture remains green (or until tic analysis shows completion of the reaction, respectively). Saturated aqueous NH4Cl solution (10 ml) is added with stirring. The organic phase is separated and the aqueous layer is extracted with diethyl ether (3×50 ml). The combined organic extracts are dried over magnesium sulfate and concentrated in vacuo. Purification of the residue by flash column chromatography (pentane/diethyl ether 5:1) affords (S)-5-(tert-butyldimethylsilyloxy)-4-methyl-pentan-1-ol 6(471 mg, 97%) as a colourless oil. 13C-NMR (100 MHz, CDCl3): δ=68.29; 63.36; 35.57; 30.24; 29.25; 25.98; 18.38; 16.77; −5.34

Provenance & Evidence