Water → Indole-3-propanol

HRID 1095510Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][CH2:17][C:18](O)=[O:19])=[CH:8]1.O.OS(O)(=O)=O>C1COCC1.CCOCC>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][CH2:17][CH2:18][OH:19])=[CH:8]1

Participants

Conditions

Temperature: 10 °C

Procedure

LiAlH4 (1.21 mg, 31.71 mmol) was initially introduced into dry THF (50 ml). A solution of 3-indolepropionic acid (2.5 g, 13.21 mmol) in dry THF (80 ml) was added dropwise to the suspension in the course of 30 min. Thereafter, the reaction mixture was heated under reflux for 3 h at 10° C. and then stirred at RT for 18. H2O (60 ml) was subsequently added, and then a mixture of conc. H2SO4 (10 ml) and H2O (30 ml). The mixture was stirred for 20 min and ether (50 ml) was finally added. The organic phase was separated off and the aqueous phase was extracted with ether (3×40 ml). The combined ethereal extracts were dried over Na2SO4 and, after filtration of the drying agent, concentrated to dryness on a rotary evaporator. 3-(1H-Indol-3-yl)propanol was obtained as a viscous oil (2.28 g, 99%).

Workup

temperatureThereafter, the reaction mixture was heated
stirringThe mixture was stirred for 20 min
customThe organic phase was separated off
extractionthe aqueous phase was extracted with ether (3×40 ml)
dry with materialThe combined ethereal extracts were dried over Na2SO4
filtrationafter filtration of the drying agent
concentrationconcentrated to dryness on a rotary evaporator

Sources & evidence

ORD record: ord-7b264548fcf44c64b4b37803d6fb25d6
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138187B2

Reaction notes

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