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

HRID 1821145
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HRID 1821145 반응식
[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]
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6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 7368
(Trifluoromethyl)benzene
용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-5d5db703235044468071285d6242b432
출처 데이터셋
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07605286B2

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