Chloromethyl Methyl Ether → HCID 10494728, compound

HRID 1884319Notes

Reaction equation

HRID 1884319 reaction equation
[CH2:1]([C:4]1[C:13]([CH3:14])=[C:12]2[C:7]([C:8]([CH3:17])([CH3:16])[CH2:9][C:10](=[O:15])[O:11]2)=[C:6]([CH3:18])[C:5]=1[OH:19])[CH:2]=[CH2:3].CCN(C(C)C)C(C)C.[CH3:29][O:30][CH2:31]Cl>C(Cl)Cl>[CH2:1]([C:4]1[C:13]([CH3:14])=[C:12]2[C:7]([C:8]([CH3:16])([CH3:17])[CH2:9][C:10](=[O:15])[O:11]2)=[C:6]([CH3:18])[C:5]=1[O:19][CH2:29][O:30][CH3:31])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 11777390HCID 11777390, compound

Product 1

HCID 10494728HCID 10494728, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Compound C (8.26 g, 31.65 mmol) and DIPEA (57.2 mL, 317.7 mmol) were dissolved in 160 mL of methylene chloride. The mixture was cooled in an ice-water bath and stirred under N2. Methoxymethyl chloride (12.2 mL, 159 mmol) was added dropwise. After the addition, the mixture was stirred at room temperature under N2 overnight. The mixture was diluted with 140 mL of methylene chloride and washed with 10% HCl solution (2×50 mL) and water (3×50 mL) and dried over MgSO4. Filtration and solvent evaporation gave a yellow residue, which was purified on a silica gel column (hexanes and ethyl acetate, 3/1, v/v) to give 8.61 g (87%) of a solid product. 1H NMR (CDCl3) δ5.96 (m, 1H), 5.07-4.95 (m, 2H), 4.90 (s, 2H), 3.63 (s, 3H), 3.47 (d, J=5.7 Hz, 2H), 2.58 (s, 2H), 2.40 (s, 3H), 2.22 (s, 3H), 1.47 (s, 6H).

Workup

  1. temperatureThe mixture was cooled in an ice-water bath
  2. additionAfter the addition
  3. stirringthe mixture was stirred at room temperature under N2 overnight
  4. washwashed with 10% HCl solution (2×50 mL) and water (3×50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationFiltration and solvent evaporation
  7. customgave a yellow residue, which
  8. customwas purified on a silica gel column (hexanes and ethyl acetate, 3/1

Sources & evidence

ORD record
ord-3dc957a94f5e4e19b7065789df1bfbb2
Source dataset
uspto-grants-2004_07
Patent number
US06764768B2

Reaction notes

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