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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
Notes
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Reaction equation

HRID 1588149 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents

2
HCID 8028TetrahydrofuranSolventHCID 22174802Benzene etherSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d1b618cb66e1473c8eb668000644d0a5
Source dataset
uspto-grants-1993_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05220042

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes