Methane, dichloromethoxy- → HCID 15516676, compound

HRID 323803Notes

Reaction equation

HRID 323803 reaction equation
[C:1]([NH:4][C:5]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH2:11][O:12][C:13](=[O:15])[CH3:14])[CH2:6][O:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2].[CH3:24][O:25]C(Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[C:1]([NH:4][C:5]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]=[O:25])=[CH:20][CH:19]=1)([CH2:11][O:12][C:13](=[O:15])[CH3:14])[CH2:6][O:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 10543752ACETAMIDE, N-[1,1-BIS[(ACETYLOXY)METHYL]-3-PHENYLPROPYL]-

Product 1

HCID 15516676HCID 15516676, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-acetamido-1, 3-diacetoxy-2-(2-phenylethyl)propane (10 g) in anhydrous dichloromethane (150 ml) were added titanium tetrachloride (15.4 ml) and dichloromethyl methyl ether (5.63 ml) under a nitrogen atmosphere at −15° C. The mixture was stirred at room temperature for 2 hours, poured into ice water and extracted with chloroform. The chloroform layer was washed with water, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; diisopropyl ether: ethyl acetate =1:1) to give the title compound (5.1 g) as a white solid, melting point 98-100° C.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform layer was washed with water
  3. dry with materiala saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent; diisopropyl ether: ethyl acetate =1:1)

Sources & evidence

ORD record
ord-628b0ac45bfb44b6a60b13cb6e5ca068
Source dataset
uspto-grants-2001_04
Patent number
US06214873B1

Reaction notes

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