Tetrahydrofuran → 2-[2,5-Dimethoxy-3,6-bis(methoxymethoxy)phenyl]ethyl 3-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]propyl ether

HRID 1588153Notes

Reaction equation

HRID 1588153 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:9]([O:10][CH2:11][O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=[C:6]([O:16][CH2:17][O:18][CH3:19])[C:5]=1[O:20][CH3:21].[H-].[Na+].O1CCCC1.I[CH2:30][CH2:31][CH2:32][C:33]1[C:38]([O:39][CH2:40][O:41][CH3:42])=[C:37]([O:43][CH3:44])[CH:36]=[C:35]([O:45][CH2:46][O:47][CH3:48])[C:34]=1[O:49][CH3:50]>CN(C)C=O.C(OCC)C>[CH3:50][O:49][C:34]1[C:35]([O:45][CH2:46][O:47][CH3:48])=[CH:36][C:37]([O:43][CH3:44])=[C:38]([O:39][CH2:40][O:41][CH3:42])[C:33]=1[CH2:32][CH2:31][CH2:30][O:1][CH2:2][CH2:3][C:4]1[C:9]([O:10][CH2:11][O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=[C:6]([O:16][CH2:17][O:18][CH3:19])[C:5]=1[O:20][CH3:21]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 137145691-(2-Hydroxyethyl)-2,5-dimethoxy-3,6-bis(methoxymethoxy)benzeneHCID 197572441-(3-Iodopropyl)-2,5-dimethoxy-3,6-bis(methoxymethoxy)benzene

Product 1

HCID 197572532-[2,5-Dimethoxy-3,6-bis(methoxymethoxy)phenyl]ethyl 3-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]propyl ether

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

374 Milligrams of 1-(2-hydroxyethyl)-2,5-dimethoxy-3,6-bis(methoxymethoxy)benzene was dissolved in 3 ml of dimethylformamide, under ice-cooling conditions, 80 mg of sodium hydride (60% dispersion) was added thereto, then 2 ml of tetrahydrofuran solution containing 527 mg of 1-(3-iodopropyl)-2,5-dimethoxy-3,6-bis(methoxymethoxy)benzene was added. The reaction mixture was heated at 50° C. in an oil bath. 6 Hours later, ice water and 100 ml of diethyl ether were added to the reaction mixture. The ether layer was washed twice with 50 ml of water, then washed twice with 50 ml of a saturated sodium chloride aqueous solution, then dried over anhydrous magnesium sulfate. This solution was concentrated under reduced pressure, and the residue obtained was purified by means of a silica gel column chromatography (diameter 3 cm×length 15 cm, eluent: 40% ethyl acetate-n-hexane mixed solvent, adsorbent: "Wakogel C-200") to obtain 484 mg of 2-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]ethyl 3 -[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]propyl ether.

Workup

  1. additionwas added
  2. additionwas added
  3. washThe ether layer was washed twice with 50 ml of water
  4. washwashed twice with 50 ml of a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThis solution was concentrated under reduced pressure
  7. customthe residue obtained
  8. customwas purified by means of a silica gel column chromatography (diameter 3 cm×length 15 cm, eluent: 40% ethyl acetate-n-hexane mixed solvent, adsorbent: "Wakogel C-200")

Sources & evidence

ORD record
ord-9b083a2a6b98427abb4af477927e812d
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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