Ethyl Acetate → Methyl 4-(2-methylindol-3-yl)butyrate

HRID 1974558Notes

Reaction equation

HRID 1974558 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11](=O)[CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=[CH:6][CH:5]=2.C(OCC)(=O)C>O1CCCC1.[Cl-].[Na+].O>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 730054Methyl 4-(2-methylindol-3-yl)-4-oxobutyrate

Product 1

HCID 10609557Methyl 4-(2-methylindol-3-yl)butyrateYield 88.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 4-(2-methylindol-3-yl)-4-oxobutyrate (2.0 g) in tetrahydrofuran (50 ml) was added a 1M solution of boran in tetrahydrofuran (16.5 ml) at 0° C. After stirred at 0° C. for 30 minutes, the mixture was poured into a mixture of ethyl acetate and brine. 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 (50 g) eluting with chloroform to give methyl 4-(2-methylindol-3-yl)butyrate (1.67 g) 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 solvent
  5. customthe residue was purified by column chromatography on silica gel (50 g)
  6. washeluting with chloroform

Sources & evidence

ORD record
ord-7cd8598994e745ee9b96caf2229f6eba
Source dataset
uspto-grants-1994_02
Patent number
US05283251

Reaction notes

Loading…