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3,6-Diethoxy-2,5-dihydropyrazine → 3,6-Diethoxy-2-{2-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-3-methylbutyl}-2,5-dihydropyrazine

HRID 252411
ノート
印刷プレビュー

反応式

HRID 252411 の反応式
C([Li])CCC.[CH2:6]([O:8][C:9]1[CH2:10][N:11]=[C:12]([O:15][CH2:16][CH3:17])[CH2:13][N:14]=1)[CH3:7].Br[CH2:19][CH:20]([CH:37]([CH3:39])[CH3:38])[CH2:21][C:22]1[CH:31]=[C:30]2[C:25]([CH:26]=[CH:27][CH:28]=[C:29]2[O:32][CH2:33][CH2:34][O:35][CH3:36])=[CH:24][CH:23]=1>O1CCCC1>[CH2:6]([O:8][C:9]1[CH:10]([CH2:19][CH:20]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]3[C:30](=[C:29]([O:32][CH2:33][CH2:34][O:35][CH3:36])[CH:28]=[CH:27][CH:26]=3)[CH:31]=2)[CH:37]([CH3:38])[CH3:39])[N:11]=[C:12]([O:15][CH2:16][CH3:17])[CH2:13][N:14]=1)[CH3:7]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 111267023,6-Diethoxy-2,5-dihydropyrazineHCID 668884037-(2-Bromomethyl-3-methylbutyl)-1-(2-methoxyethoxy)naphthaleneHCID 178418339Butyllithium

生成物 1

HCID 668877873,6-Diethoxy-2-{2-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-3-methylbutyl}-2,5-dihydropyrazine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-20 °C

実験手順

3.03 ml of n-butyllithium (1.6M in hexane) are added dropwise at −40° C. to the suspension of 0.884 g of 3,6-diethoxy-2,5-dihydropyrazine in 12 ml of tetrahydrofuran. After 20 minutes, a solution of 1.265 g of 7-(2-bromomethyl-3-methylbutyl)-1-(2-methoxyethoxy)naphthalene in 5 ml of tetrahydrofuran is added dropwise. The reaction mixture is stirred further at −40″C. for 30 minutes, then warmed to −20° C. over 1 hour. After 18 hours, the reaction mixture is concentrated by evaporation—the residue is partitioned between ethyl acetate and water. The aqueous phase is extracted with ethyl acetate (2×)—the combined organic phases are washed successively with water (2×) and brine, dried over sodium sulphate and concentrated by evaporation. The crude title compound is identified on the basis of the Rf value from the residue.

後処理

  1. waitfor 30 minutes
  2. waitAfter 18 hours
  3. concentrationthe reaction mixture is concentrated by evaporation—the residue
  4. customis partitioned between ethyl acetate and water
  5. extractionThe aqueous phase is extracted with ethyl acetate (2×)—the combined organic phases
  6. washare washed successively with water (2×) and brine
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-44ff97a902354401ac764936c965ac76
出典データセット
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07868036B2

反応ノート

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