Ethanol → 3-(6-Methoxy-1H-Indol-4-yl)-3-phenyl-propionaldehyde

HRID 1716694Notes

Reaction equation

C([O:3][C:4](=O)[CH2:5][CH:6]([C:13]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]2[C:14]=1[CH:15]=[CH:16][NH:17]2)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.CC(C[AlH]CC(C)C)C.CCO.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:23][O:22][C:20]1[CH:19]=[C:18]2[C:14]([CH:15]=[CH:16][NH:17]2)=[C:13]([CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][CH:4]=[O:3])[CH:21]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a −78° C. solution of 3-(6-Methoxy-1H-Indol-4-yl)-3-phenyl-propionic acid ethyl ester CXVII (0.39 g, 1.2 mmol) in DCM (10 ml) was added DIBALH (1M in hexane, 4.0 ml, 4.0 mmol). After stirring for 90 minutes at −78° C., more DIBALH (1M in hexane, 1.2 ml, 1.2 mmol) was added. The resulting mixture was stirred for 2.25 hours, after which EtOH (2 ml) and a saturated solution of NaHCO3 (2 ml) were added. The mixture was then stirred at room temperature for 30 min, filtered, and the filter cake was washed with EtOAc. The filtrate was concentrated and washed with a saturated solution of NaHCO3, dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc) affording 3-(6-Methoxy-1H-Indol-4-yl)-3-phenyl-propionaldehyde CXVIII as a colorless syrup (0.27 g, 82% yield).

Workup

stirringThe resulting mixture was stirred for 2.25 hours
stirringThe mixture was then stirred at room temperature for 30 min
filtrationfiltered
washthe filter cake was washed with EtOAc
concentrationThe filtrate was concentrated
washwashed with a saturated solution of NaHCO3
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
custompurified via flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record: ord-c057ca2fb8a242988488dd7b8b63fcd5
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803830B2

Reaction notes

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