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

HRID 862560

反応式

HRID 862560 の反応式
[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

参加物

7

反応物 4

HCID 962WaterHCID 14798Sodium Hydroxide2 回HCID 2736972Methyl 1,2,3,4-tetrahydroquinoline-2-carboxylateHCID 21226445Aluminium lithium hydride

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-edf4c1abe13443eb986d015ad3f7fc81
出典データセット
uspto-grants-1998_02
特許番号
US05719152

関連ノート

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