Acetic Acid → (5-Hydroxy-indol-1-yl)-acetic acid ethyl ester

HRID 490752Notes

Reaction equation

HRID 490752 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15]CC3C=CC=CC=3)=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:2].C(O)(=O)C.[H][H]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 59897880HCID 59897880, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57675474(5-Hydroxy-indol-1-yl)-acetic acid ethyl esterYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

(5-Benzyloxy-indol-1-yl)-acetic acid ethyl ester (3.49 g, 11.31 mmol) is dissolved in EtOH (50 mL) and glacial acetic acid is added (2.0 mL). Palladium on carbon (20% by wt., 0.700 g) is then added to the homogenous solution, and a hydrogen filled balloon is connected to the round bottom flask. A vacuum is created within the flask until the ethanol began to bubble, and the hydrogen allowed to enter the flask; this procedure is repeated three times, then the reaction is left to stir at room temperature overnight. Upon completion, the reaction is diluted with DCM (200 mL), and water (100 mL) is added. The mixture is filtered through a celite plug and the two phases are separated. The organic layer is washed with brine (2×75 mL), then dried over anhydrous magnesium sulfate, and concentrated to yield the title compound (2.42 g) in 98% yield. The residual acetic acid is removed by flash column chromatography. 1H NMR (DMSO-d6, 400 MHz): δ 1.18 (t, J=7.34 Hz, 3H), 4.12 (q, J=6.85 Hz, 2H), 4.99 (s, 2H), 5.73 (s, 1H), 6.23 (d, J=2.94 Hz, 1H), 6.60 (dd, J1=1.96 Hz, J2=8.80 Hz, 1H), 6.84 (d, J=2.45 Hz, 1H), 7.12 (d, J=8.80 Hz, 1H), 7.19 (d, J=2.94 Hz, 2H); MS (ES, m/z):C12H13NO3: 220.21(M++1), 218.7(M+−1).

Workup

  1. customto bubble
  2. waitthe reaction is left
  3. additionUpon completion, the reaction is diluted with DCM (200 mL), and water (100 mL)
  4. additionis added
  5. filtrationThe mixture is filtered through a celite plug
  6. customthe two phases are separated
  7. washThe organic layer is washed with brine (2×75 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8c0ea94a5a424d4f8f95a31fb118d6db
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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