Toluene → (1H-indol-5-yl)methanol

HRID 381761

反応式

HRID 381761 の反応式
[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>C1COCC1>[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a mechanically stirred solution of 1H-Indole-5-carboxylic acid (5-1, 20.01 g, 124 mmol) in THF (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 ethylacetate and saturated aqueous NaHCO3. The organic layer was washed with brine, separated, dried (MgSO4) and 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) δ8.24 (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).

後処理

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

出典と根拠

ORDレコード
ord-55365ee09fd44db58c3ba35c40139ab1
出典データセット
uspto-grants-2001_10
特許番号
US06306874B1

関連ノート

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