1-Methoxynaphthalene → HCID 15617937、化合物

HRID 703917ノート

反応式

HRID 703917 の反応式
C([Li])CCC.[CH3:6][O:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1.Br[CH2:19][CH2:20][CH2:21][CH2:22][Cl:23].[Cl-].[NH4+]>C1CCCCC1>[Cl:23][CH2:22][CH2:21][CH2:20][CH2:19][C:9]1[CH:10]=[CH:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1[O:7][CH3:6]

参加物

6

反応物 4

HCID 166681-MethoxynaphthaleneHCID 25517Ammonium ChlorideHCID 813641-Bromo-4-chlorobutaneHCID 178418339Butyllithium

生成物 1

HCID 15617937HCID 15617937、化合物収率 39%

試薬・触媒・溶媒 1

HCID 8078Cyclohexane溶媒2 回

実験手順

A solution of N,N,N',N'-tetramethylenediamine (18.12 mL, 0.120 mole) in cyclohexane (36 mL) was treated with n-butyllithium (1.55M in hexane; 79.8 mL, 0.123 mole) at room temperature. A solution of 1-methoxynaphthalene (17.4 mL, 0.120 mole) in cyclohexane (20 mL) was added over 30 minutes, and the resulting solution was stirred for 1.5 hours. It was then cooled to 0°, and 1-bromo-4-chlorobutane (27.0 mL, 0.234 mole) was added over 15 minutes. The mixture was warmed to room temperature and stirred for 17 hours, then poured into saturated aqueous ammonium chloride and extracted with ethyl acetate. The crude product was chromatographed with 98:2 hexane/ether to provide the title compound (11.60 g, 39%) as a pale yellow oil.

後処理

  1. temperatureIt was then cooled to 0°
  2. stirringstirred for 17 hours
  3. extractionextracted with ethyl acetate
  4. customThe crude product was chromatographed with 98:2 hexane/ether

出典と根拠

ORDレコード
ord-355c88f0ad1c48f4adbccaf6c649e74a
出典データセット
uspto-grants-1991_01
特許番号
US04985435

反応ノート

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