Ethyl Acetate → (1-Methyl-1H-indazol-5-YL)methanol

HRID 1498900노트

반응식

HRID 1498900 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17](OCC)=[O:18])=[CH:14][CH:15]=2)[CH:10]=[N:9]1.C(OCC)(=O)C>O1CCCC1.C(=O)(O)[O-].[Na+]>[CH3:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][OH:18])=[CH:14][CH:15]=2)[CH:10]=[N:9]1

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 68642052HCID 68642052, 화합물

생성물 1

HCID 44119264(1-Methyl-1H-indazol-5-YL)methanol수율 66.1%

시약·촉매·용매 2

HCID 516892Sodium Bicarbonate촉매2회HCID 8028Tetrahydrofuran용매2회

실험 절차

Lithium aluminum hydride (300 mg, 7.83 mmol) was suspended in tetrahydrofuran (20 ml); and under an ice cooling, a solution (10 ml) of ethyl 1-methyl-1H-indazole-5-carboxylate (800 mg, 3.92 mmol) prepared in the Step 4-1-3-A in tetrahydrofuran was slowly added thereto. After the mixture was stirred under an ice cooling for 30 minutes, 5 drops of a saturated sodium bicarbonate solution were slowly added to the mixture. Ethyl acetate was added to the mixture, and 5 drops of a saturated sodium bicarbonate solution was further added thereto. The precipitate was removed by filtration, and the filtrate was concentrated. The concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give the title compound (420 mg, 66%) as a light-brown powder.

후처리

  1. additionwas slowly added
  2. additionwas further added
  3. customThe precipitate was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customThe concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-7915fe22a53a4de9a72f63468c919adc
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09200008B2

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