Chloromethyl Methyl Ether → HCID 131719456, compound

HRID 1957377Notes

Reaction equation

HRID 1957377 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][S:6][C:5]([S:8][CH3:9])=[N:4]1.[CH:10](N(C(C)C)CC)(C)C.Cl[CH2:20][O:21]C>ClCCl>[CH3:20][O:21][C@:3]1([CH2:2][O:1][CH3:10])[CH2:7][S:6][C:5]([S:8][CH3:9])=[N:4]1

Participants

5

Procedure

3.14 g of Compound (6) obtained in the step (a) and 6.7 ml of diisopropylethylamine were dissolved in 40 ml of dry dichloromethane solution. 2.33 g of chloromethylmethyl ether was added to the above mixture under ice-cooling and the reaction mixture was stirred for 1 hour under the same condition and for 15 hours at room temperature. After the reaction, the reaction mixture was washed with water, saturated sodium bicarbonate solution and saturated saline solution, and dried over magnesium sulfate. After removal of the solvent, the resulting residue was purified by silica gel column chromatography (chloroform-ethyl acetate) to give 1.42 g (36%) of 4(R)-methoxy-methyloxymethyl-2-methylthio-1,3-thiazoline [Compound (7)].

Workup

  1. temperaturecooling
  2. customAfter the reaction
  3. washthe reaction mixture was washed with water, saturated sodium bicarbonate solution and saturated saline solution
  4. dry with materialdried over magnesium sulfate
  5. customAfter removal of the solvent
  6. customthe resulting residue was purified by silica gel column chromatography (chloroform-ethyl acetate)

Sources & evidence

ORD record
ord-148a41974d16473e815f3aa1163bd3d1
Source dataset
uspto-grants-1998_07
Patent number
US05783703

Reaction notes

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