ChemicalBook CAS DataBase List INDOLE-4-METHANOL

INDOLE-4-METHANOL synthesis

14synthesis methods

Product Name:INDOLE-4-METHANOL
CAS Number:1074-85-7
Molecular formula:C9H9NO
Molecular Weight:147.17

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Yield: 99%

Reaction Conditions:

with sodium hydroxide in tetrahydrofuran;water

Steps:

38.A Example 38
Step A: To a mixture of lithium aluminum hydride (1.3 g, 34 mmol) in THF (200 mL), methyl 4-indole carboxylate (3.0 g, 17 mmol) in THF (100 mL) was added dropwise at room temperature. The reaction mixture was stirred at room temperature for 2 h and then quenched with ethyl acetate. The mixture was treated with water (1.3 mL), 15% NaOH (1.3 mL) and water (3.9 mL), and then filtered. The filtrate was concentrated in vacuo to afford the crude 4-(hydroxymethyl)-indole (2.5 g, 99%): ¹H NMR (500 MHz, CDCl₃) δ 8.29 (br s, 1H), 7.34 (d, J=9.0 Hz, 1H), 7.16-7.22 (m, 2H), 7.12 (d, J 7.0 Hz, 1H), 6.67 (t, J=1.0 Hz, 1H), 4.98 (d, J=4.2 Hz, 2H); CI MS m/z=147 [C₉H₉NO+H]⁺.

References:

Beck, James P.;Pechulis, Anthony D.;Harms, Arthur E. US2002/91134, 2002, A1