methyl (S)-lactate → methyl (S)-2-(methoxymethoxy)propionate

HRID 1821145Notes

Reaction equation

HRID 1821145 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C@H:2]([CH3:4])[OH:3].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.ClC[C:27]([O:29][CH2:30]OC)=C.C(=O)([O-])O.[Na+]>C1(C(F)(F)F)C=CC=CC=1>[CH3:27][O:29][CH2:30][O:3][C@@H:2]([CH3:4])[C:1]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 94386methyl (S)-lactateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 106782943-Chloro-2-(methoxymethoxy)prop-1-ene

Product 1

HCID 10582920methyl (S)-2-(methoxymethoxy)propionateYield 84%

Reagents, catalysts & solvents 1

HCID 7368(Trifluoromethyl)benzeneSolvent

Procedure

Methyl L-lactate (208 mg, 2 mmol) was dissolved in benzotrifluoride (2.0 mL), pyridinium p-toluenesulfonate (PPTS, 50 mg, 0.2 mmol) was added and then 2-(chloromethyl)-3,5-dioxahexa-1-ene (manufactured by Tokyo Kasei Kogyo Co., Ltd., 327 mg, 2.4 mmol) was added, and the mixture was stirred at room temperature for 24 hrs. Saturated aqueous sodium hydrogencarbonate solution (3 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (4 mL). The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution (2 mL) and dried over anhydrous magnesium sulfate (0.5 g), and the solvent was evaporated under reduced pressure to give methyl (S)-2-(methoxymethoxy)propionate (248 mg, yield 84%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (4 mL)
  2. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution (2 mL)
  3. dry with materialdried over anhydrous magnesium sulfate (0.5 g)
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5d5db703235044468071285d6242b432
Source dataset
uspto-grants-2009_10
Patent number
US07605286B2

Reaction notes

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