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

HRID 268818Notes

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-propionaldeyde 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-38a76b1bef7d4893b069ed677a9d4b05
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446118B2

Reaction notes

Loading…