Tributyltin Chloride → HCID 23658640, compound

2.00 g (14.5 mmol) of 3-methoxybenzyl alcohol were dissolved in 40 ml of dry benzene. At 0° C., 19.91 ml (31.9 mmol, 2.2 eq.) of a 1.6 molar n-BuLi solution were slowly added dropwise, where the white suspension formed after addition of one equivalent of n-BuLi changed its color to dark red during the addition of the second equivalent. Stirring at RT was continued for another 2 hours, and 5.1 ml (18.8 mmol, 1.3 eq.) of tributyltin chloride were then added at 0° C. The mixture was stirred at RT overnight, and 40 ml of saturated NH4Cl solution were then added and the mixture was extracted three times with 70 ml of EA. After washing of the organic phase with saturated NaCl solution and drying over MgSO4, the solvent was removed. The crude product was purified by column chromatography (reversed-phase silica RP-18, MeCN), which gave 4.83 g (11.3 mmol, 78%) of 3-methoxy-2-(tributylstannyl)benzyl alcohol as a colorless oil. In a further experiment, a yield of 60% was obtained.

1. customwhere the white suspension formed
2. additiondark red during the addition of the second equivalent
3. stirringThe mixture was stirred at RT overnight
4. extractionthe mixture was extracted three times with 70 ml of EA
5. washAfter washing of the organic phase with saturated NaCl solution
6. dry with materialdrying over MgSO4
7. customthe solvent was removed
8. customThe crude product was purified by column chromatography (reversed-phase silica RP-18, MeCN), which

ORD record

ord-a564e7ec011648c5bc6a3e4e4be87a0f

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07763740B2