1-(Chloromethoxy)-2-methoxyethane → HCID 14700405, compound

HRID 1651655Notes

Reaction equation

HRID 1651655 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH:7]([OH:9])[CH3:8].C(N(CC)C(C)C)(C)C.[CH3:19][O:20][CH2:21][CH2:22][O:23][CH2:24]Cl>C(Cl)Cl>[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH:7]([O:9][CH2:19][O:20][CH2:21][CH2:22][O:23][CH3:24])[CH3:8]

Participants

5

Reactant 3

HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 23050267HCID 23050267, compound

Product 1

HCID 14700405HCID 14700405, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-bromo-3-(l-hydroxyethyl)thiophene (97.5 g, 0.47 mol) in dry methylene chloride (400 ml) was cooled in ice and N,N-diisopropylethylamine (68.2 g, 0.517 mol) was added followed by methoxyethoxymethYl chloride (64.4 g, 0.517 mol). The solution was stirred at room temperature over night. The dark solution was washed with water, 3N HCl, saturated NaHCO3 and finally with water. The solution was dried over anhydrous Na2SO4 filtered and concentrated in vacuo at room temperature. A dark amber oil was obtained (123.1 g). The impure product was distilled and the product was collected at 108-116° C. at 0.7 mm Hg. to give 91.1 g (66%) of colorless liquid. NMR supported the structure.

Workup

  1. washThe dark solution was washed with water, 3N HCl, saturated NaHCO3 and finally with water
  2. dry with materialThe solution was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo at room temperature
  5. customA dark amber oil was obtained (123.1 g)
  6. distillationThe impure product was distilled
  7. customthe product was collected at 108-116° C. at 0.7 mm Hg

Sources & evidence

ORD record
ord-bf5ef5f878414079ae6ce26899adc3be
Source dataset
uspto-grants-1990_05
Patent number
US04929637

Reaction notes

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