Toluene → (1H-indol-5-yl)methanol

HRID 1061704Notes

Reaction equation

HRID 1061704 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10](O)=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1(C)C=CC=CC=1>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][OH:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 742801H-Indole-5-Carboxylic AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 2773458(1H-indol-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mechanically stirred solution of 1H-Indole-5-carboxylic acid (3-1, 20.01 g, 124 mmol) in tetrahydrofuran (500 mL) was added at ambient temperature slowly a solution of 1M-LAH in toluene (186 mL, 186 mmol, 1.5 equiv). The reaction mixture was heated at reflux for 1 h, quenched with ice, partitioned between EA and saturated aqueous NaHCO3. The organic layer was washed with brine, separated, dried (MgSO4) ans concentrated in vacuo. The crude product solidified upon standing under the reduced pressure. The crude solid was suspended in hexanes (200 mL) and ethyl acetate (10 mL), stirred overnight, collected by filtration and air-dried to afford the desired product as a light brown solid. 1H NMR (400 MHz, CDCl3) δ 8.24 (br s, 1H), 7.62 (s, 1H), 7.36 (d, 1H, J=8.4 Hz), 7.23 (d, 1H, J=8.4 Hz), 7.20 (s, 1H), 6.54 (s, 1H), 4.75 (s, 2H), 1.68 (s, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 h
  3. customquenched with ice
  4. custompartitioned between EA and saturated aqueous NaHCO3
  5. washThe organic layer was washed with brine
  6. customseparated
  7. dry with materialdried (MgSO4)
  8. concentrationans concentrated in vacuo
  9. filtrationcollected by filtration
  10. customair-dried

Sources & evidence

ORD record
ord-d749e1b51ed14ec183107f4cc909879f
Source dataset
uspto-grants-2005_11
Patent number
US06960590B2

Reaction notes

Loading…