Ethyl Acetate → HCID 19757259, compound

HRID 1588133Notes

Reaction equation

HRID 1588133 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH2:10][O:11][CH3:12])=[CH:7][C:6]([O:13][CH3:14])=[C:5]([O:15][CH2:16][O:17][CH3:18])[C:4]=1[CH2:19][CH2:20][C:21]([OH:23])=O.C(OCC)(=O)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl.C(N(CC)CC)C>[CH3:30][S:31]([O:23][CH2:21][CH2:20][CH2:19][C:4]1[C:5]([O:15][CH2:16][O:17][CH3:18])=[C:6]([O:13][CH3:14])[CH:7]=[C:8]([O:9][CH2:10][O:11][CH3:12])[C:3]=1[O:2][CH3:1])(=[O:33])=[O:32]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 19757239HCID 19757239, compound

Product 1

HCID 19757259HCID 19757259, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

700 Milligrams of 3-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]propionyl alcohol was dissolved in 20 ml of anhydrous methylene chloride, under argon gas stream condition, 0.21 ml of methanesulfonyl chloride, 0.3 ml of triethylamine were added thereto under ice-cooled condition. The temperature of the reaction mixture was elevated to room temperature, then the reaction mixture was stirred continuously for 12 hours. 100 Milliliters of ethyl acetate was added to the reaction mixture, and the organic layer was washed with water, a saturated sodium chloride aqueous solution, then concentrated to yield 700 mg of 3-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]propyl methanesulfonate was obtained as a mesylate. Colorless oily substance.

Workup

  1. additionwere added
  2. temperatureunder ice-cooled condition
  3. customwas elevated to room temperature
  4. washthe organic layer was washed with water
  5. concentrationa saturated sodium chloride aqueous solution, then concentrated

Sources & evidence

ORD record
ord-0ea7b460e20b46c4a479d8fd519850aa
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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