Chloride → HCID 20284858, compound

HRID 127564Notes

Reaction equation

HRID 127564 reaction equation
[CH2:1]1[CH2:13][O:12][C:3]([CH3:11])([CH2:4][CH2:5][CH2:6][CH:7]([CH3:10])[CH2:8][OH:9])[O:2]1.C([Li])CCC.CO[CH2:21][CH2:22][O:23][CH2:24]Cl.[Cl-].[O:27]1CCC[CH2:28]1>>[CH2:13]1[CH2:1][O:2][C:3]([CH3:11])([CH2:4][CH2:5][CH2:6][CH:7]([CH3:10])[CH2:8][O:9][CH2:28][O:27][CH:22]([O:23][CH3:24])[CH3:21])[O:12]1

Participants

6

Reactant 5

HCID 312ChlorideHCID 8028TetrahydrofuranHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 14078297HCID 14078297, compoundHCID 178418339Butyllithium

Product 1

HCID 20284858HCID 20284858, compound

Conditions

Temperature
-78 °C

Procedure

6,6-Ethylenedioxy-2-methyl-heptanol (2.0 g) is dissolved in anhydrous tetrahydrofuran (35 ml) and cooled to -78° C. under nitrogen. n-Butyllithium (0.68 g) is added and the solution is warmed to 0° C. Methoxyethoxymethyl chloride (1.59 g) is added and the reaction stirred at 0° C. for 1.5 hours. An additional 1.59 g of the chloride is added and stirring is continued at 0° C. for 2 hours. The tetrahydrofuran is evaporated in vacuo and the residue is partitioned between ether and brine. The ether extract is dried (Na2SO4) and the solvent is evaporated in vacuo to give 6,6-ethylenedioxy-1-methoxyethoxymethoxy-2-methylheptane. The compound is dissolved in acetone (40 ml) and 10% hydrochloric acid (2.0 ml) is added and the resulting solution is stirred for two hours. A saturated sodium bicarbonate solution (50 ml) is added, and the resulting precipitate filtered and the filtrate evaporated in vacuo. The residue is partitioned between ether and brine and the ether extract is dried (Na2SO4) and evporated in vacuo. The residue is chromatographed on silica (solvent: ethyl acetate/hexane) to give 1-methoxyethoxymethoxy-2-methyl-6-oxo-heptane as a colorless liquid, nmr (CDCl3,δ) 0.9 (d, CH3CH), 2.12 (s, CH3C=O), 2.4 (t, --CH2C=O, 3.3-3.8 (m, --OCH3, ##STR44## --OCH2CH2O), 4.66 (s, 2H, --OCH2O--).

Workup

  1. temperaturethe solution is warmed to 0° C
  2. stirringstirring
  3. waitis continued at 0° C. for 2 hours
  4. customThe tetrahydrofuran is evaporated in vacuo
  5. customthe residue is partitioned between ether and brine
  6. extractionThe ether extract
  7. dry with materialis dried (Na2SO4)
  8. customthe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-10e684383de8445ab64add96c60ea15f
Source dataset
uspto-grants-1981_03
Patent number
US04256644

Reaction notes

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