Ammonium Chloride → (E)-3-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]-2-butenol

HRID 378380ノート

反応式

HRID 378380 の反応式
[CH3:1][CH:2]([N:4]1[C:13]2[C:8](=[CH:9][C:10](/[C:14](/[CH3:21])=[CH:15]/[C:16](OCC)=[O:17])=[CH:11][CH:12]=2)[CH2:7][CH2:6][CH2:5]1)[CH3:3].[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+]>O1CCCC1.C1(C)C=CC=CC=1>[CH3:3][CH:2]([N:4]1[C:13]2[C:8](=[CH:9][C:10](/[C:14](/[CH3:21])=[CH:15]/[CH2:16][OH:17])=[CH:11][CH:12]=2)[CH2:7][CH2:6][CH2:5]1)[CH3:1]

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 10517412Ethyl (E)-3-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]-2-butenoateHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 10658040(E)-3-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]-2-butenol収率 76.1%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-70 °C

実験手順

1.0 g of ethyl (E)-3-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]-2-butenoate prepared in Example 1 was dissolved in 20 ml of tetrahydrofuran. The obtained solution was cooled to -70° C., followed by the gradual addition of 7.0 ml (10.5 mmol) of a 1.5M solution of diisobutylaluminum hydride in toluene. The obtained mixture was stirred for 2 hours, followed by the addition of an aqueous solution of ammonium chloride. The obtained mixture was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and concentrated in a vacuum to give 650 mg of the title compound as a colorless oil.

後処理

  1. extractionThe obtained mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with a saturated aqueous solution of common salt
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in a vacuum

出典と根拠

ORDレコード
ord-0b91ce4d6d184fa7a31dcfc627ba7a0f
出典データセット
uspto-grants-2000_02
特許番号
US06030964

反応ノート

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