1-(Chloromethoxy)-2-methoxyethane → HCID 14590840, compound

HRID 373642Notes

Reaction equation

HRID 373642 reaction equation
[OH:1][C@H:2]([C@@H:5]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[CH:3]=[CH2:4].C(N(C(C)C)CC)(C)C.[CH3:30][O:31][CH2:32][CH2:33][O:34][CH2:35]Cl>C(Cl)Cl>[CH3:30][O:31][CH2:32][CH2:33][O:34][CH2:35][O:1][C@H:2]([C@@H:5]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)[CH:3]=[CH2:4]

Participants

5

Reactant 3

HCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 13891107HCID 13891107, compound

Product 1

HCID 14590840HCID 14590840, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the resultant compound from Example 6 (2.51 g, 8.84 mmol) in methylene chloride (20 ml) was added diisopropylethylamine (4.60 ml, 26.4 mmol) and methoxyethoxychloromethane (3.00 ml, 26.3 mmol). After stirring at room temperature for 24 h the mixture was concentrated, diluted with ethyl acetate, washed with 0.5M H3PO4, saturated NaHCO3 solution, then brine, dried over Na2SO4, and evaporated. Chromatography on silica gel with ethyl acetate/ hexane mixtures afforded 2.63 g (80%) of the desired product as an oil. EI-MS: M+ =371.

Workup

  1. concentrationwas concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with 0.5M H3PO4, saturated NaHCO3 solution
  4. dry with materialbrine, dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-c83f694e1904441aa55fa01afc28c109
Source dataset
uspto-grants-1992_11
Patent number
US05164388

Reaction notes

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