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Methyl iodide → 1,4-Dimethoxy-2,5-bis(methoxymethoxy)-3-methyl-6-{5-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]pentyl}benzene

HRID 1588149
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HRID 1588149 반응식
[CH3:1][O:2][C:3]1[C:8]([O:9][CH2:10][O:11][CH3:12])=[CH:7][C:6]([O:13][CH3:14])=[C:5]([O:15][CH2:16][O:17][CH3:18])[C:4]=1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[C:29]([O:30][CH2:31][O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=[C:26]([O:36][CH2:37][O:38][CH3:39])[C:25]=1[O:40][CH3:41].[CH3:42]N(C)P(=O)(N(C)C)N(C)C.C([Li])(CC)C.CI>O1CCCC1.C(OCC)C.C1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]2[C:29]([O:30][CH2:31][O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=[C:26]([O:36][CH2:37][O:38][CH3:39])[C:25]=2[O:40][CH3:41])=[C:5]([O:15][CH2:16][O:17][CH3:18])[C:6]([O:13][CH3:14])=[C:7]([CH3:42])[C:8]=1[O:9][CH2:10][O:11][CH3:12]
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참가 물질

7

반응물 4

HCID 6328Methyl iodideHCID 12679HexamethylphosphoramideHCID 136460702,2'-Pentamethylene-bis[1,4-dimethoxy-3,6-bis(methoxymethoxy)benzene]HCID 178418400CID 53628100

생성물 1

HCID 136460751,4-Dimethoxy-2,5-bis(methoxymethoxy)-3-methyl-6-{5-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]pentyl}benzene

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
HCID 22174802Benzene ether용매

실험 절차

140 Milligrams of 2,2'-pentamethylene-bis[1,4-dimethoxy-3,6-bis(methoxymethoxy)benzene] was dissolved in 5 ml of anhydrous tetrahydrofuran under argon gas stream conditions, then 0.5 ml of hexamethylphosphoric triamide was added to this solution and the mixture was cooled in a dry ice-acetone bath. Next, 0.23 ml of sec-butyllithium (1.4M, cyclohexane solution) was added dropwise to the reaction mixture and stirred for 1 hour. Then, 0.06 ml of methyl iodide was added dropwise thereto under cooling in a dry ice-acetone bath for 12 hours with stirring. The solvent was removed by evaporation under reduced pressure, to the residue obtained was added 100 ml of a mixed solvent of diethyl ether-benzene (1:1), and the organic layer was washed with water then with a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. The dried solution was concentrated under reduced pressure to obtain 100 mg of 1,4-dimethoxy-2,5-bis(methoxymethoxy)-3-methyl-6-{5-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]pentyl}benzene. Colorless needles crystals.

후처리

  1. temperaturethe mixture was cooled in a dry ice-acetone bath
  2. temperatureunder cooling in a dry ice-acetone bath for 12 hours
  3. stirringwith stirring
  4. customThe solvent was removed by evaporation under reduced pressure, to the residue
  5. customobtained
  6. washthe organic layer was washed with water
  7. dry with materialwith a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate
  8. concentrationThe dried solution was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d1b618cb66e1473c8eb668000644d0a5
출처 데이터셋
uspto-grants-1993_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05220042

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