1H-Indole-1-carboxylic acid, 5-(hydroxyMethyl)-, 1,1-diMethylethyl ester Chemical Properties

Boiling point:

396.0±34.0 °C(Predicted)

Density 

1.14±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

14.37±0.10(Predicted)

Safety Information

HS Code 

2933998090

1H-Indole-1-carboxylic acid, 5-(hydroxyMethyl)-, 1,1-diMethylethyl ester Usage And Synthesis

Synthesis

General procedure for the synthesis of tert-butyl 5-(hydroxymethyl)-1H-indole-1-carboxylate from tert-butyl 5-formyl-1H-indole-1-carboxylate: firstly, tert-butyl 5-formyl-1H-indole-1-carboxylate (12.23 mmol) was dissolved in methanol (30 mL) to obtain a solution. To this solution, sodium tetrahydroborate (0.463 g, 12.23 mmol) was slowly added at 0 °C. The reaction mixture was stirred continuously at 0 °C for 3 h, followed by stirring at room temperature overnight. After completion of the reaction, the resulting solution was diluted with water (40 mL) and extracted with ethyl acetate (3 x 30 mL). The organic layers were combined, washed sequentially with aqueous sodium carbonate and brine, dried over anhydrous sodium sulfate, and concentrated in vacuum to afford tert-butyl 5-(hydroxymethyl)-1H-indole-1-carboxylate (2.5 g, 10.11 mmol, 83% yield) as a yellow oil.LCMS analysis showed m/z = 270.3 [M + Na]+.

References

[1] Journal of the American Chemical Society, 2017, vol. 139, # 20, p. 6847 - 6850
[2] Patent: WO2017/216726, 2017, A1. Location in patent: Page/Page column 955

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