Diethyl Ether → HCID 19757195, compound

HRID 1588152Notes

Reaction equation

HRID 1588152 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][O:11][CH3:12])[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[O:15][CH2:16][O:17][CH3:18].C([Li])(CC)C.I[CH2:25][CH2:26][CH2:27][CH2:28][C:29]1[C:34]([O:35][CH2:36][O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=[C:31]([O:41][CH2:42][O:43][CH3:44])[C:30]=1[O:45][CH3:46].C(OCC)C>O1CCCC1.CN(C)P(=O)(N(C)C)N(C)C>[CH3:1][O:2][C:3]1[C:4]([O:15][CH2:16][O:17][CH3:18])=[CH:5][C:6]([O:13][CH3:14])=[C:7]([O:9][CH2:10][O:11][CH3:12])[C:8]=1[CH2:25][CH2:26][CH2:27][CH2:28][C:29]1[C:34]([O:35][CH2:36][O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=[C:31]([O:41][CH2:42][O:43][CH3:44])[C:30]=1[O:45][CH3:46]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 10061046HCID 10061046, compoundHCID 19757191HCID 19757191, compoundHCID 178418400CID 53628100

Product 1

HCID 19757195HCID 19757195, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
-78 °C

Procedure

280 Milligrams (1.08 mmoles) of 1,4-dimethoxy-2,5-bis(methoxymethoxy)benzene was dissolved in a mixed solvent of 5 ml of tetrahydrofuran with 1 ml of hexamethylphosphoric triamide, then this solution was cooled to -78° C. in a dry ice-acetone bath. To this cooled solution was added 1.08 ml (1.21 mmoles) of secbutyllithium (1.21 M, cyclohexane solution) and the mixture was stirred for 30 minutes, then 2 ml of tetrahydrofuran solution containing 440 mg (1.0 mmole) of 1-(4-iodobutyl)-2,5-dimethoxy-3,6-bis(methoxymethoxy)benzene was added thereto and stirred for 12 hours. The reaction mixture was concentrated, to the residue obtained was added 60 ml of diethyl ether, and washed twice with water, then washed twice with a saturated sodium chloride aqueous solution, then dried over anhydrous magnesium sulfate. The dried diethyl ether solution was concentrated under reduced pressure, the residue obtained was purified by means of a silica gel column chromatography (diameter 2 cm×length 20 cm, eluent: 20% ethyl acetate-benzene) to obtain 467 mg of 2,2'-tetramethylenebis[1,4-dimethoxy-3,6-bis(methoxymethoxy)benzene]. Colorless oily substance.

Workup

  1. additionwas added
  2. stirringstirred for 12 hours
  3. concentrationThe reaction mixture was concentrated, to the residue
  4. customobtained
  5. washwashed twice with water
  6. washwashed twice with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationThe dried diethyl ether solution was concentrated under reduced pressure
  9. customthe residue obtained
  10. customwas purified by means of a silica gel column chromatography (diameter 2 cm×length 20 cm, eluent: 20% ethyl acetate-benzene)

Sources & evidence

ORD record
ord-20bd47b7ad864742aa4d09bc99f10b90
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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