Hydrochloric Acid → HCID 10705928, compound

HRID 1974559Notes

Reaction equation

B(F)(F)F.CCOCC.[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[C:20](=O)[CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24].[BH4-].[Na+].Cl>O1CCCC1.C(OCC)(=O)C.CC(C)=O>[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24]

Participants

Conditions

Temperature: 25 °C

Procedure

Boron trifluoride etherate (4.2 ml) was added to a mixture of methyl 4-(5-chloroindol-3-yl)-4-oxobutyrate (3.00 g) and sodium borohydride (0.855 g) in tetrahydrofuran (100 ml) at 25° C. over 20 minutes. After the mixture was stirred at 25° C. for 3 hours, acetone (5 ml) was added. The reaction mixture was poured into a mixture of ethyl acetate and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. After evaporation of solvent, the residue was purified by column chromatography on silica gel (200 ml) eluting with chloroform and by recrystallization from a mixture of ethyl acetate and hexane to give methyl 4-(5-chloroindol-3-yl)butyrate (989 mg) as colorless crystals.

Workup

customThe organic layer was separated
washwashed with water and brine
dry with materialdried over magnesium sulfate
customAfter evaporation of solvent
customthe residue was purified by column chromatography on silica gel (200 ml)
washeluting with chloroform and by recrystallization from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record: ord-7d66c51b75484341ba5c36f317013387
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05283251

Reaction notes

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