Tetrahydrofuran → 6-Hydroxymethylindole

HRID 1362049Notes

Reaction equation

HRID 1362049 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10](O)=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.C1COCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>O.CO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][OH:11])[CH:8]=2)[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 5952301H-indole-6-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 27734596-HydroxymethylindoleYield 96.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Indole-6-carboxylic acid (1.0 g, 6.2 mmol) was dissolved into anhydrous THF (20 mL) under argon. Lithium aluminum hydride (494 mg, 13 mmol) was added portionwise and the mixture was stirred overnight. The mixture was cooled to 0° C. and ethyl acetate (10 mL) was carefully added, followed by methanol (5 mL) and water (5 mL). The mixture was stirred for 30 min. and filtered through celite. The solution was concentrated and dissolved into ethyl acetate (200 mL) and washed with brine (2×20 mL), dried over MgSO4 and concentrated to afford the title compound as a brown oil (880 mg, 96%). 1H NMR (300 MHz, CDCl3) δ 8.30 (s, 1H), 7.58 (d, J=8.1 Hz, 1H), 7.23 (d, J=1.1 Hz, 1H), 7.13-7.05 (m, 2H), 6.51-6.49 (m, 1H), 4.70 (s, 2H).

Workup

  1. stirringThe mixture was stirred for 30 min.
  2. filtrationfiltered through celite
  3. concentrationThe solution was concentrated
  4. dissolutiondissolved into ethyl acetate (200 mL)
  5. washwashed with brine (2×20 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-296a7f6e533242ceab35946e5b3b9458
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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