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

HRID 490752

反応式

HRID 490752 の反応式
[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]

参加物

6

反応物 3

HCID 176Acetic AcidHCID 59897880HCID 59897880、化合物HCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒2 回

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-8c0ea94a5a424d4f8f95a31fb118d6db
出典データセット
uspto-grants-2009_05
特許番号
US07528160B2

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