Triethylamine → 3-(2-Methoxybenzyloxy)benzyl methanesulfonate

HRID 2254423Notes

Reaction equation

HRID 2254423 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=[O:11].[BH4-].[Na+].[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(N(CC)CC)C>C(O)C.C(Cl)Cl>[CH3:21][S:22]([O:11][CH2:10][C:9]1[CH:12]=[CH:13][CH:14]=[C:7]([O:6][CH2:5][C:4]2[CH:15]=[CH:16][CH:17]=[CH:18][C:3]=2[O:2][CH3:1])[CH:8]=1)(=[O:24])=[O:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 4311764Sodium borohydrideHCID 197446743-[(2-Methoxybenzyl)oxy]benzaldehyde

Product 1

HCID 197446853-(2-Methoxybenzyloxy)benzyl methanesulfonateYield 95.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

530 mg of 3-(2-methoxybenzyloxy)benzyl alcohol obtained by reducing 3-(2-methoxybenzyloxy)benzaldehyde with sodium borohydride in ethanol was dissolved in 8 ml of methylene chloride. The solution was stirred at -5° to 0° C., 0.20 ml of methanesulfonyl chloride and 0.65 ml of triethylamine were added. The mixture was stirred at this temperature for 5 minutes. The reaction mixture was diluted with methylene chloride, washed with a saturated aqueous solution of sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give 660 mg (yield 95.3%) of the captioned compound as a colorless oil.

Workup

  1. stirringThe mixture was stirred at this temperature for 5 minutes
  2. washwashed with a saturated aqueous solution of sodium hydrogen carbonate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a6523f97b4714d6395647080b33a8420
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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