Boron trifluoride etherate → Ethyl 4-[3-(3-nitrobenzyl)indol-1-yl]butyrate

HRID 249154Notes

Reaction equation

HRID 249154 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][CH:28]=1)[C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:10]=1)=O)([O-:3])=[O:2].[BH4-].[Na+].B(F)(F)F.CCOCC.C(OCC)(=O)C>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][CH:28]=1)[CH2:7][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:10]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 10547793Ethyl 4-[3-(3-nitrobenzoyl)indol-1-yl]butyrate

Product 1

HCID 19024737Ethyl 4-[3-(3-nitrobenzyl)indol-1-yl]butyrateYield 35.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-[3-(3-nitrobenzoyl)indol-1-yl]butyrate (0.5 g) in tetrahydrofuran (10 ml) were added sodium borohydride (99.4 mg) and boron trifluoride etherate (0.485 ml) at -25° C., and the mixture was stirred at the same temperature for 2 hours. The mixture was poured into a mixture of ethyl acetate and ice water. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. After evaporation of the solvent, the residue was chromatographed on silica gel (25 g) eluting with a mixture of ethyl acetate and hexane (1:4) to give ethyl 4-[3-(3-nitrobenzyl)indol-1-yl]butyrate (173 mg) as a yellow oil.

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation of the solvent
  5. customthe residue was chromatographed on silica gel (25 g)
  6. washeluting with a mixture of ethyl acetate and hexane (1:4)

Sources & evidence

ORD record
ord-d5b05f02ad3247ef84eb4ad05375a1f2
Source dataset
uspto-grants-1993_05
Patent number
US05212320

Reaction notes

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