1-Heptanol, 7-[[(1,1-dimethylethyl)diphenylsilyl]oxy]- synthesis

Yield: 89%

Reaction Conditions:

Stage #1:1,7-heptandiol with sodium hydride in tetrahydrofuran;oil at 0;Inert atmosphere;
Stage #2:tert-butylchlorodiphenylsilane with tetra-(n-butyl)ammonium iodide in tetrahydrofuran;oil at 20; for 12 h;Inert atmosphere;

Steps:

7-(tert-butyldiphenylsilyloxy) heptan-1-ol
To a solution of 1,7- heptane diol (10.0 g, 75.7 mmol) in THF (100 mL) was added sodium hydride (1.81 g, 60% dispersion in oil, 75.7 mmol) portion wise at 0 oC under nitrogen atmosphere. Stir the reaction mixture at 0 oC for 15 min. Then TBDPSCl (20.8 g, 75.7 mmol) was added slowly to the reaction mixture followed by addition of TBAI (2.79 g, 7.57 mmol). The stirring was continued for additional 12 h at room temperature. The reaction mixture was quenched at 0 oC by saturated aqueous NH4Cl solution (200 mL). THF was removed under reduced pressure and the product was extracted from aqueous layer with EtOAc (3 x 500 mL).The combined organic layers were washed with brine (2 x 100 mL) and dried over Na2SO4(anhydrous), filtered and concentrated in vacuo. Purification by column chromatography (Silica gel) of crude residue eluting with 30-35% EtOAc in hexane afforded mono-protected alcohol as a colorless oil. Yield : 25.1 g, 89 % 1H NMR (400 MHz, CDCl3) : d 7.64-7.61 (m, 4H), 7.38-7.31 (m, 6H), 3.66-3.56 (m, 4H), 1.58-1.48 (m, 3H), 1.41-1.25 (m, 7H), 1.04 (s, 9H).

References:

Kumaraswamy, Gullapalli;Ramakrishna, Gajula;Sridhar, Balasubramanian [Tetrahedron Letters,2011,vol. 52,# 15,p. 1778 - 1782] Location in patent:supporting information; experimental part