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

HRID 326381Notes

Reaction equation

HRID 326381 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 20 (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-93bcffd22bb64300be672400d82beb6a
Source dataset
uspto-grants-1993_12
Patent number
US05268374

Reaction notes

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