Triethylamine → 1,1-Dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl methanesulfonate

HRID 1907008Notes

Reaction equation

HRID 1907008 reaction equation
[CH3:1][O:2][C:3]([O:19][CH3:20])([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[CH:8]=1)[CH:4]([OH:6])[CH3:5].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[CH3:28][S:29]([O:6][CH:4]([CH3:5])[C:3]([O:19][CH3:20])([O:2][CH3:1])[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[CH:8]=1)(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 113003471,1-Dimethoxy-1-(6-methoxy-2-naphthyl)propan-2-ol

Product 1

HCID 127563301,1-Dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

The crude oil, 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)propan-2-ol, from Example 8 is dissolved in 200 ml of methylene chloride and to that mixture is added 13.2 g of triethylamine. The reaction mixture is cooled to 5° C. and 11.0 g of methanesulfonyl chloride is added slowly, maintaining the temperature between 5°-10° C. The precipitation of triethylamine hydrochloride crystals is observed. After the addition of the methanesulfonyl chloride has been completed, the reaction mixture is stirred for an additional one-half hour. Then the solution is filtered to remove the triethylamine hydrochloride crystals and the filtrate is poured into 200 ml of water. The organic layer is separated and dried over magnesium sulfate. Evaporation of the organic layer under reduced pressure yields 30.4 g of crude 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl methanesulfonate as an oil.

Workup

  1. temperaturemaintaining the temperature between 5°-10° C
  2. customThe precipitation of triethylamine hydrochloride crystals
  3. additionAfter the addition of the methanesulfonyl chloride
  4. filtrationThen the solution is filtered
  5. customto remove the triethylamine hydrochloride crystals
  6. additionthe filtrate is poured into 200 ml of water
  7. customThe organic layer is separated
  8. dry with materialdried over magnesium sulfate
  9. customEvaporation of the organic layer under reduced pressure

Sources & evidence

ORD record
ord-90601dca77984ee8be7254c8277f3aaf
Source dataset
uspto-grants-1987_03
Patent number
US04654438

Reaction notes

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