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Triethylsilane → Dimethyl-3-(tetrahydro-furan-3-yloxy)-propionic acid methyl ester

HRID 1046443
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HRID 1046443 반응식
[CH3:1][O:2][C:3](=[O:13])[C:4]([CH3:12])([CH3:11])[CH2:5][O:6][Si](C)(C)C.[O:14]1[CH2:18][CH2:17][C:16](=O)[CH2:15]1.C([SiH](CC)CC)C.C([O-])(O)=O.[Na+]>[N+](C)([O-])=O>[CH3:1][O:2][C:3](=[O:13])[C:4]([CH3:12])([CH3:11])[CH2:5][O:6][CH:16]1[CH2:17][CH2:18][O:14][CH2:15]1
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참가 물질

6

반응물 4

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 5293923-OxotetrahydrofuranHCID 866501662,2-Dimethyl-3-trimethylsilanyloxy-propionic acid methyl ester

생성물 1

HCID 58114071Dimethyl-3-(tetrahydro-furan-3-yloxy)-propionic acid methyl ester수율 89.5%

시약·촉매·용매 1

HCID 6375
Nitromethane
용매

실험 절차

2,2-Dimethyl-3-trimethylsilanyloxy-propionic acid methyl ester (478 mg, 2.34 mmol) was added to a solution of dihydro-furan-3-one (168 mg, 1.95 mmol) and FeCl3 (16 mg, 0.097 mmol) in nitromethane (6.0 mL) at 0° C. Triethylsilane (0.374 mL, 2.33 mmol) was added and the reaction was warmed to room temperature and stirred for 2 h. Sat. NaHCO3 was added and the reaction was extracted with dichloromethane. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated to give a pale liquid. Purification by flash column chromatography on silica gel using 30% ethyl acetate in hexanes provided dimethyl-3-(tetrahydro-furan-3-yloxy)-propionic acid methyl ester (353 mg, 75%) as a colorless liquid.

후처리

  1. extractionthe reaction was extracted with dichloromethane
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give a pale liquid
  7. customPurification by flash column chromatography on silica gel using 30% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-6d5022cbbad94e489dcc14d88265b5b8
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08569302B2

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