Methanol → (1H-indol-2-yl)methanol

HRID 7172

反応式

HRID 7172 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]1[C:16](O)=[O:17].CO>C1COCC1>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]1[CH2:16][OH:17]

参加物

5

反応物 3

HCID 887MethanolHCID 72899Indole-2-carboxylic acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 98783(1H-indol-2-yl)methanol収率 68%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

LiAlH4 (1.0 m in THF, 5.0 mL, 5.0 mmol) was slowly added to a solution of indole-2-carboxylic acid (403 mg, 2.5 mmol) in dry THF (18 mL) at 0° C. The resultant yellow solution was warmed to room temperature and stirred for 18 hours. MeOH (0.5 mL) was added and the solution concentrated under reduced pressure (3×). The resultant orange syrup was partially dissolved in CHCl3 (150 mL) and washed consecutively with H2O (10 mL) and NH4Cl (10 mL). The aqueous layer was extracted with CHCl3 (2×25 mL). The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure. Purification by column chromatography on silica gel (100% CH2Cl2) afforded the desired alcohol (250 mg, 68%) as a yellow solid. 1H NMR (CDCl3) δ 4.84 (s, 2H), 6.42 (d, 1H, J=0.9 Hz), 7.11–7.20 (m, 2H), 7.36 (d, 1H, J=7.5 Hz), 7.59 (d, 1H, J=7.5 Hz), 8.31 (br s, 1H).

後処理

  1. concentrationthe solution concentrated under reduced pressure (3×)
  2. dissolutionThe resultant orange syrup was partially dissolved in CHCl3 (150 mL)
  3. washwashed consecutively with H2O (10 mL) and NH4Cl (10 mL)
  4. extractionThe aqueous layer was extracted with CHCl3 (2×25 mL)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography on silica gel (100% CH2Cl2)

出典と根拠

ORDレコード
ord-7a1d7d25ee944766945434c34744294c
出典データセット
uspto-grants-2006_08
特許番号
US07084155B2

関連ノート

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