Indole synthesis

15synthesis methods

Product Name:Indole
CAS Number:120-72-9
Molecular formula:C8H7N
Molecular Weight:117.15

Obtained from the 220 to 260°C boiling fraction of coal tar or by heating sodium phenyl-glycine-o-carboxylate with NaOH, saturating the aqueous solution of the melt with CO2 and finally reducing with sodium amalgam; can be prepared also by the reduction of indoxyl, indoxyl carboxylic acid or indigo.

70957-04-9 Synthesis

1H-Indole, 1-(2,2-dimethyl-1-oxopropyl)-

70957-04-9
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120-72-9
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Yield:120-72-9 100%

Reaction Conditions:

with n-butyllithium;diisopropylamine in tetrahydrofuran;hexanes at -78 - 45; for 2 h;Inert atmosphere;

Steps:

4.3. General procedures for the deprotection of N-pivaloylindoles

General procedure: Method A: To 1.6 M solution of butyllithium in hexanes (2 equiv) was added dropwise a stirred solution of diisopropylamine (2 equiv) in dry THF (2 mL×mmol) at 0 °C, under an argon atmosphere. Stirring was continued for 10 min at 0 °C, and the solution of LDA thus prepared was added via cannula to a stirred solution of the suitable 1-pivaloyl derivative (1 equiv) in THF (2 mL×mmol), under an argon atmosphere at -78 °C. When addition was complete, the reaction mixture was heated in an oil bath at 40-45 °C for 2 h, cooled and poured onto a saturated aqueous NH₄Cl solution (30 mL), which was then extracted with CH₂Cl₂ (3×15 mL). The combined organic layers were dried over Na₂SO₄ and evaporated, and the residue was chromatographed on silica gel, eluting with 9:1 EtOAc-petroleum ether. Evaporation of the mobile phase yielded the deprotected indole, which was identical in all respects to the commercially available sample employed as starting material for the protection reaction.

References:

Ruiz, Míriam;Sánchez, J. Domingo;López-Alvarado, Pilar;Menéndez, J. Carlos [Tetrahedron,2012,vol. 68,# 2,p. 705 - 710] Location in patent:experimental part

59-48-3 Synthesis