Methanol → (1H-indol-2-yl)methanol

HRID 7172

반응식

HRID 7172 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7a1d7d25ee944766945434c34744294c
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084155B2

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