Ammonium Hydroxide → 2-Di-n-propylamino-8-(fur-3-yl)-1,2,3,4-tetrahydronaphthalene

HRID 22134

反応式

HRID 22134 の反応式
[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8](Br)[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].[Mg].Br[C:21]1[CH:25]=[CH:24][O:23][CH:22]=1.[OH-].[NH4+]>C1COCC1.BrC(Br)C.C1(C)C=CC=CC=1.C1C=CC([P]([Ni]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Ni](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([C:21]3[CH:25]=[CH:24][O:23][CH:22]=3)[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3]

参加物

11

反応物 4

HCID 14923Ammonium HydroxideHCID 891643-Bromofuran2 回HCID 5462224MagnesiumHCID 145295648-Bromo-2-dipropylamino-1,2,3,4-tetrahydronaphthalene

生成物 1

HCID 152224292-Di-n-propylamino-8-(fur-3-yl)-1,2,3,4-tetrahydronaphthalene収率 84.1%

試薬・触媒・溶媒 6

HCID 112011,1-Dibromoethane触媒HCID 178418751HCID 178418751、化合物触媒HCID 178420538HCID 178420538、化合物触媒2 回HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

2-Di-n-propylamino-8-bromo-1,2,3,4-tetrahydronaphthalene (1.0 g; 3.2 mmol) was dissolved in 20 ml of THF, and 94 mg (3.9 mmol) of magnesium shavings were added. The mixture was refluxed, and a couple of drops of dibromoethane were added to initiate Grignard formation. The mixture was refluxed for one hour after which it was added to a solution of 0.58 ml (6.4 mmol) of 3-bromofuran and 36 mg (0.03 mmol) of Ni(PPh3)4 in 20 ml of toluene that had been cooled to 0° C. after stirring at room temperature for one hour. The mixture was stirred at room temperature for three hours after which an additional 0.58 ml of 3-bromofuran and 35 mg of Ni(PPh3)4 were added. When the reaction failed to proceed further, 210 mg (0.3 mmol) Ni(PPh3)2Cl2 was added, and the mixture was stirred overnight at room temperature. The mixture then was poured into water and the pH adjusted to 10 with ammonium hydroxide. The mixture was extracted with methylene chloride, dried over sodium sulfate, and evaporated to give 0.8 g of a residue.

後処理

  1. temperatureThe mixture was refluxed
  2. temperatureThe mixture was refluxed for one hour after which it
  3. additionwere added
  4. stirringthe mixture was stirred overnight at room temperature
  5. extractionThe mixture was extracted with methylene chloride
  6. dry with materialdried over sodium sulfate
  7. customevaporated

出典と根拠

ORDレコード
ord-d34262a676634d269babbf51150d3970
出典データセット
uspto-grants-1995_06
特許番号
US05426226

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