1-(Chloromethoxy)-2-methoxyethane → HCID 89590808, compound

HRID 522351Notes

Reaction equation

HRID 522351 reaction equation
[Li]CCCC.[CH:6]1([S:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:11])=[O:10])[CH2:8][CH2:7]1.[CH3:20][O:21][CH2:22][CH2:23][O:24][CH2:25]Cl>C1COCC1>[CH3:20][O:21][CH2:22][CH2:23][O:24][CH2:25][C:6]1([S:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])(=[O:11])=[O:10])[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 20773763tert-Butyl (cyclopropanesulfonyl)carbamateHCID 178418339Butyllithium

Product 1

HCID 89590808HCID 89590808, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

BuLi 2.5 M in hexanes (7.53 ml) was added dropwise to the solution of tert-butyl (cyclopropylsulfonyl)carbamate (1.81 g) in THF (40 ml) at −78° C. This solution was stirred at −78° C. for 1 hour then 2-methoxyethoxymethyl chloride (1.85 ml) was added dropwise. The reaction was allowed to warm to room temperature and was stirred for 3 days. The solvent was evaporated under reduced pressure and the residue was diluted with ethyl acetate. At this point, HCl (1 M) was added and the mixture was extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography (ISCO, 0 to 100% ethyl acetate in hexanes) to give the desired product (0.630 g) as a clear oil. LRMS (ES+) m/z 332.2 (M+Na)+.

Workup

  1. temperatureto warm to room temperature
  2. stirringwas stirred for 3 days
  3. customThe solvent was evaporated under reduced pressure
  4. additionthe residue was diluted with ethyl acetate
  5. additionAt this point, HCl (1 M) was added
  6. extractionthe mixture was extracted with ethyl acetate (3×)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent was evaporated under reduced pressure
  11. customThe residue was purified by flash chromatography (ISCO, 0 to 100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3d44ed735a3749908cf7a60864a2f622
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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