ChemicalBook CAS DataBase List 10-Bromodecanol

10-Bromodecanol synthesis

13synthesis methods

Product Name:10-Bromodecanol
CAS Number:53463-68-6
Molecular formula:C10H21BrO
Molecular Weight:237.18

Decane, 1-bromo-10-[(2-methoxyethoxy)methoxy]-

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Yield:53463-68-6 95%

Reaction Conditions:

Stage #1: C₁₄H₂₉BrO₃with [2,2]bipyridinyl;trimethylsilyl trifluoromethanesulfonate in dichloromethane at 0; for 0.5 h;Inert atmosphere;
Stage #2: with water in diethyl ether;dichloromethane at 20; for 5 h;Inert atmosphere;chemoselective reaction;

Steps:

4.5. Deprotection of MOM, MEM, BOM, or SEM ether by TMSOTf (TESOTf)/2,2'-bipyridyl combination

General procedure: TMSOTf or TESOTf (2.0 equiv) was added dropwise to a solution of MOM, MEM, BOM, or SEM ether (1, 3-5) and 2,2'-bipyridyl (3.0 equiv) in CH₂Cl₂ (0.2 M) at 0 °C under N₂. The reaction mixture was stirred at the same temperature. After checking the disappearance of the starting material on TLC (30 min), H₂O (2 mL/mmol) and Et₂O (2 mL/mmol) were added to the reaction mixture and vigorously stirred. After disappearance of the high polar component was ascertained by TLC, the reaction mixture was extracted with CH₂Cl₂. The organic layer was washed with 3.5% HCl aq twice (for removal of 2,2'-bipyridyl) and with satd NaHCO₃ aq. The combined organic layer was dried over Na₂SO₄, filtered, and evaporated in vacuo. The residue was purified by flash column chromatography to give an alcohol 2. Silica gel 60 N (neutral) was used for the purification of substrate having TBS or Tr ethers instead of Merck Silica gel 60. Compounds 2e^[31a], 2f^[4a], 2g^31b, 2h^31c, 2i^31d, 2j^31e, and 2k²⁸ are known compounds.

References:

Fujioka, Hiromichi;Minamitsuji, Yutaka;Kubo, Ozora;Senami, Kento;Maegawa, Tomohiro [Tetrahedron,2011,vol. 67,# 16,p. 2949 - 2960] Location in patent:experimental part

112-47-0 Synthesis