ChemicalBook CAS DataBase List 5-HEXADECANONE

5-HEXADECANONE synthesis

11synthesis methods

Product Name:5-HEXADECANONE
CAS Number:41903-81-5
Molecular formula:C16H32O
Molecular Weight:240.42

693-03-8 Synthesis

693-03-8
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$153.00/50mL

63252-22-2
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41903-81-5
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$39.20/5g

103-49-1 Synthesis

103-49-1
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Yield:41903-81-5 89% ，103-49-1 86%

Reaction Conditions:

Stage #1: C₂₆H₃₇NOwith 2,6-di-tert-butyl-4-methylpyridine;trifluoromethylsulfonic anhydride in dichloromethane at -78 - 0; for 2 h;Inert atmosphere;
Stage #2: n-butyl magnesium bromide in diethyl ether;dichloromethane at -78; for 2 h;Inert atmosphere;chemoselective reaction;

Steps:

4.2. General procedure for the direct transformation of tertiary amides into ketones and amines

General procedure: Tf₂O (1.2 equiv) was added dropwise to a cooled (-78 °C) solution of amide 5 (1.0 equiv) and DTBMP (1.2 equiv) in CH₂Cl₂ (5 mL). The reaction was allowed warming to 0 °C over 2 h. A solution of Grignard reagent (1.0 equiv) in Et₂O was added dropwise to the resultant mixture at -78 °C, and the mixture was stirred at the same temperature for 2 h. The reaction mixture was then quenched with an aqueous solution of 15% HCl (5 mL). The organic layer was separated and the aqueous phase was extracted with diethyl ether (3×5 mL). The combined organic layers were washed with brine, dried over anhydrous Na₂SO₄, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to afford the desired ketone 1. To isolate the corresponding amine, the aqueous solution layer was basified with an aqueous solution of 15% NaOH (6 mL), and extracted with dichloromethane (3×10 mL), the combined organic layers were dried over anhydrous Na₂SO₄, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to afford the desired amine 6.

References:

Huang, Pei-Qiang;Wang, Yu;Xiao, Kai-Jiong;Huang, Ying-Hong [Tetrahedron,2015,vol. 71,# 24,art. no. 26677,p. 4248 - 4254]

693-03-8 Synthesis

693-03-8
60 suppliers
$153.00/50mL