Tetrahydrofuran → 3-(2-Hydroxyethyl)-1H-indole-2-carboxylic acid

HRID 858278Notes

Reaction equation

HRID 858278 reaction equation
[C:1]1(=[O:14])[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH2:3][O:2]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.C1C[O:18]CC1>>[OH:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:1]([OH:14])=[O:18]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 3261784,9-dihydro-3H-pyrano[3,4-b]indol-1-one

Product 1

HCID 166410173-(2-Hydroxyethyl)-1H-indole-2-carboxylic acid

Procedure

To a solution of 4,9-dihydro-3H-pyrano[3,4-b]indol-1-one (Arch. Pharm., 1987, 320, 1202–1209, 5.225 g, 27.9 mmol) in THF (25 mL) was added deoxygenated 3 N KOH (25 mL). The mixture was stirred at room temperature for 4.5 hours. The reaction mixture was washed with EtOAc, acidified with 1 N HCl, and extracted with EtOAc. The organic extract was dried over MgSO4 and concentrated to give 5.589 g of 3-(2-hydroxyethyl)-1H-indole-2-carboxylic acid as a solid. This material was used for the next reaction without further purification: 1H NMR (DMSO-d6) δ 3.26 (t, J=7.5 Hz, 2H), 3.63 (t, J=7.5 Hz, 2H), 7.08 (t, J=7.5 Hz, 1H), 7.26 (t, J=7.7 Hz, 1H), 7.43 (d, J=8.3 Hz, 1H), 7.69 (d, J=8.1 Hz, 1H). Anal. Calcd. for C11H11NO3.0.1 EtOAc: C., 63.98; H, 5.56; N, 6.54. Found: C, 63.90; H, 5.57; N, 6.46.

Workup

  1. customdeoxygenated 3 N KOH (25 mL)
  2. washThe reaction mixture was washed with EtOAc
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. dry with materialwas dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-82251ce25f4148beb22d85fd063c2b42
Source dataset
uspto-grants-2006_12
Patent number
US07148250B2

Reaction notes

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