Diethyl Ether → 2-Methoxyethoxymethyl ether

HRID 2286751

Reaction equation

HRID 2286751 reaction equation
CC(C[CH2:7][OH:8])CCO.C([Li])CCC.[CH3:14][O:15][CH2:16][CH2:17][O:18][CH2:19]Cl.C[CH2:22][O:23][CH2:24][CH3:25].[O:26]1CCCC1>O>[CH3:14][O:15][CH2:16][CH2:17][O:18][CH2:19][O:26][CH2:7][O:8][CH2:25][CH2:24][O:23][CH3:22]

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 205243-Methyl-1,5-pentanediolHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 178418339Butyllithium

Product 1

HCID 218834272-Methoxyethoxymethyl ether

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3.54 g (30 mmol) of 3-methyl-1,5-pentanediol in 30 ml of dry tetrahydrofuran (THF) at 0° was added 19.2 ml (30 mmol) of 1.56 M n-butyllithium. After 30 min, 3.74 g (30 mmol) of β-methoxyethoxymethyl chloride was added and the reaction was stirred overnight. The reaction was poured into ether and water. The aqueous phase was back-extracted twice with ether. Combined ether layers were washed with sat. NaCl solution and were dried over calcium sulfate. The crude product was placed on 1 m×20 cm prep. SiO2 plates which were then developed with 40% ethyl acetate/hexane. Removal of the second least polar band gave the monoether derivative of 3-methyl-1,5-pentanediol (II).

Workup

  1. extractionThe aqueous phase was back-extracted twice with ether
  2. washCombined ether layers were washed with sat. NaCl solution
  3. dry with materialwere dried over calcium sulfate
  4. customRemoval of the second least polar band

Sources & evidence

ORD record
ord-cbd814ede4cc492082c0efcadf65bbc9
Source dataset
uspto-grants-1981_05
Patent number
US04267363

Linked notes

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