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

HRID 858278ノート

反応式

HRID 858278 の反応式
[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]

参加物

3

反応物 2

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-82251ce25f4148beb22d85fd063c2b42
出典データセット
uspto-grants-2006_12
特許番号
US07148250B2

反応ノート

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