1,3-Dibromopropane → 5,6,7,8-Tetrahydro-1-nitro-2-(3-bromopropoxy)naphthalene

HRID 2393298ノート

反応式

HRID 2393298 の反応式
C(=O)([O-])[O-].[K+].[K+].[Br:7][CH2:8][CH2:9][CH2:10]Br.[OH:12][C:13]1[CH:22]=[CH:21][C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[C:14]=1[N+:23]([O-:25])=[O:24]>CN(C)C=O>[N+:23]([C:14]1[C:15]2[CH2:16][CH2:17][CH2:18][CH2:19][C:20]=2[CH:21]=[CH:22][C:13]=1[O:12][CH2:10][CH2:9][CH2:8][Br:7])([O-:25])=[O:24]

参加物

5

反応物 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 49137365,6,7,8-Tetrahydro-1-nitro-2-naphthalenol

生成物 1

HCID 189755045,6,7,8-Tetrahydro-1-nitro-2-(3-bromopropoxy)naphthalene収率 67.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

N,N-dimethylformamide (180 ml), potassium carbonate (37.8 g, 0.273 mol), and 1,3-dibromopropane (93 ml, 0.916 mol) were added to 2-hydroxy-5,6,7,8-tetrahydro-1-nitronaphthalene (17.6 g, 0.091 mol) and the mixture was stirred at 70° C. for 4 hours. The precipitated salts were removed by filtration, and then the solvent was evaporated and the residue was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The residue was purified by silica gel chromatography (Wako Gell C-300: 500 g, eluent: ethyl acetate/hexane=1/20) to give 5,6,7,8-tetrahydro-1-nitro-2-(3-bromopropoxy)naphthalene (19.4 g).

後処理

  1. customThe precipitated salts were removed by filtration
  2. customthe solvent was evaporated
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified by silica gel chromatography (Wako Gell C-300: 500 g, eluent: ethyl acetate/hexane=1/20)

出典と根拠

ORDレコード
ord-c4cb0050bb6f4f3f81ba1e388453dfb5
出典データセット
uspto-grants-1998_09
特許番号
US05807860

反応ノート

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