Water → (1,2,3,4-Tetrahydroquinolin-2-yl)methanol

HRID 862560

반응식

HRID 862560 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9]([CH:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12]1)=O.[OH-].[Na+].O>C1COCC1.C(OCC)C>[OH:8][CH2:9][CH:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12]1

참가 물질

7

반응물 4

HCID 962WaterHCID 14798Sodium Hydroxide2회HCID 2736972Methyl 1,2,3,4-tetrahydroquinoline-2-carboxylateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 15052240(1,2,3,4-Tetrahydroquinolin-2-yl)methanol수율 106.9%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매3회

실험 절차

To a suspension of LiAlH4 (8.3 g, 0.22 mol) in THF (200 mL) was added dropwise 2-methoxycarbonyltetrahydroquinoline (42 g, 0.22 mol) in THF (200 mL) at 0° C. The mixture was stirred for 3 h at room temperature and refluxed for 0.5 h. The excess reagent was decomposed by addition of aqueous sodium hydroxide in THF. To the mixture was added 1N aqueous NaOH, water, and diethyl ether, successively. The organic layer was separated, washed with brine, dried over magnesium sulfate, and concentrated to give 38.4 g of 2-hydroxymethyltetrahydroquinoline (quant).

후처리

  1. temperaturerefluxed for 0.5 h
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-edf4c1abe13443eb986d015ad3f7fc81
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05719152

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