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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
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HRID 252411 반응식
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]
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-20 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-44ff97a902354401ac764936c965ac76
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07868036B2

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