1-(Chloromethoxy)-2-methoxyethane → HCID 86708407, compound

HRID 402712Notes

Reaction equation

HRID 402712 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([C:6]1[O:7][CH2:8][C:9](=[O:16])[C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:5].C(N(C(C)C)CC)(C)C.[CH3:26][O:27][CH2:28][CH2:29][O:30][CH2:31]Cl>ClCCl.O>[CH3:26][O:27][CH2:28][CH2:29][O:30][CH2:31][O:1][CH2:2][CH2:3][N:4]([C:6]1[O:7][CH2:8][C:9](=[O:16])[C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:5]

Participants

6

Reactant 3

HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 86708408HCID 86708408, compound

Product 1

HCID 86708407HCID 86708407, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-[(2-hydroxyethyl)-N-methylamino]-4-oxo-4,5-dihydrofuran-3-carboxylate (0.5 g, 2.18 mmol) which similarly prepared according to the procedure described in the Example 74, Fourth step in dichloromethane (6.0 mL) that cooled with ice bath, diisopropylethylamine (0.75 mL, 4.36 mmol) then 2-methoxyethoxymethyl chloride (0.5 mL, 4.36 mmol) were added. The reaction mixture was allowed to warm to ambient temperature and stirred for 16 h. The reaction mixture was diluted with water, extracted with ethyl acetate for 3 times. The organic layer was dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel(hexane/ethyl acetate) to afford ethyl 2-({2-[(2-methoxyethoxy)methoxy]ethyl}-N-methylamino)-4-oxo-4,5-dihydrofuran-3-carboxylate as oil (0.31 g, y. 46%).

Workup

  1. temperaturecooled with ice bath
  2. extractionextracted with ethyl acetate for 3 times
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel(hexane/ethyl acetate)

Sources & evidence

ORD record
ord-78be3acbcc32434eb81a0f252fe87698
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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